JPS54106472A - Preparation of 4, 5, 6, 7-tetrahydro-benzimidazoline-2-thione - Google Patents
Preparation of 4, 5, 6, 7-tetrahydro-benzimidazoline-2-thioneInfo
- Publication number
- JPS54106472A JPS54106472A JP1147278A JP1147278A JPS54106472A JP S54106472 A JPS54106472 A JP S54106472A JP 1147278 A JP1147278 A JP 1147278A JP 1147278 A JP1147278 A JP 1147278A JP S54106472 A JPS54106472 A JP S54106472A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- acidic substance
- compound
- thiourea
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- JKCWEUIGTMTRMK-UHFFFAOYSA-N 1,3,4,5,6,7-hexahydrobenzimidazole-2-thione Chemical compound C1CCCC2=C1N=C(S)N2 JKCWEUIGTMTRMK-UHFFFAOYSA-N 0.000 title 1
- 230000002378 acidificating effect Effects 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000000126 substance Substances 0.000 abstract 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- 238000007259 addition reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- CHPSWOWDEYXTFU-UHFFFAOYSA-N n-(2-aminocyclohexylidene)hydroxylamine Chemical compound NC1CCCCC1=NO CHPSWOWDEYXTFU-UHFFFAOYSA-N 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- INQKOYIQWPOADU-UHFFFAOYSA-N (2-hydroxyiminocyclohexyl)thiourea Chemical compound NC(=S)NC1CCCCC1=NO INQKOYIQWPOADU-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 abstract 1
- 229940092714 benzenesulfonic acid Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Abstract
PURPOSE: To obtain the title compound which is an intermediate for medicines in simple procedures in high yield, by treating a specific compound, readily prepared through addition reaction between 2-amino-cyclohexanone oxime and a thioisocyanate, with an acidic substance.
CONSTITUTION: A N-(2-hydroxyimino-cyclohexyl)-thiourea of formula I: (R is alkyl, allyl, or aralkyl group) is brought into contact with an acidic substance, e.g. hydrogen chloride, hydrogen bromide, sulfuric or benzenesulfonic acid, at 0W 150°C, preferably 10W100°C to give the objective compound of formula II. The thiourea of formula I is obtained by addition reaction of 2-amino-cyclohexanone oxime with a thiocyanate of formula IV according to the well-known method. Preferably, the amount of the acidic substance is 0.01 mole or more per mole of the compound of formula I.
COPYRIGHT: (C)1979,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1147278A JPS54106472A (en) | 1978-02-06 | 1978-02-06 | Preparation of 4, 5, 6, 7-tetrahydro-benzimidazoline-2-thione |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1147278A JPS54106472A (en) | 1978-02-06 | 1978-02-06 | Preparation of 4, 5, 6, 7-tetrahydro-benzimidazoline-2-thione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS54106472A true JPS54106472A (en) | 1979-08-21 |
Family
ID=11779005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1147278A Pending JPS54106472A (en) | 1978-02-06 | 1978-02-06 | Preparation of 4, 5, 6, 7-tetrahydro-benzimidazoline-2-thione |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS54106472A (en) |
-
1978
- 1978-02-06 JP JP1147278A patent/JPS54106472A/en active Pending
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