Phosgene → HCID 13742718, compound

HRID 1733143Notes

Reaction equation

HRID 1733143 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:6]=1[C:7]#[N:8].[C:13](Cl)(Cl)=[O:14].C[C@H]1CO[C@@]2(O[C@H]3C[C@H]4[C@@H]5CC=C6C[C@@H](O)CC[C@]6(C)[C@H]5CC[C@]4(C)[C@H]3[C@@H]2C)CC1>ClC1C=CC=CC=1>[C:7]([C:6]1[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])=[CH:4][S:3][C:2]=1[N:1]=[C:13]=[O:14])#[N:8]

Participants

5

Reactant 3

HCID 6371Phosgene3×HCID 99474DiosgeninHCID 5968662-Amino-4-(1,1-dimethylethyl)-3-thiophenecarbonitrile

Product 1

HCID 13742718HCID 13742718, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

A solution of 90 g (0.5 mole) of 2-amino-3-cyano-4-tert.-butyl-thiophene in 300 ml of chlorobenzene was added dropwise to a solution of 150 g of phosgene in 1.5 liters of chlorobenzene at 0°-5° C. Thereafter, the mixture was slowly heated to the boil, while passing further phosgene in, and excess phosgene was then driven off by passing dry nitrogen in. For working up, the solvent was stripped off under reduced pressure and the residue was distilled. 62 g of 3-cyano-4-tert.-butyl-thien-2-yl isocyanate, which boiled at 163° C. under a pressure of 20 mm Hg, were obtained in this manner.

Workup

  1. temperatureThereafter, the mixture was slowly heated to the boil
  2. distillationthe residue was distilled

Sources & evidence

ORD record
ord-24e22ecf6aa34398bd29d444aced0dc2
Source dataset
uspto-grants-1980_12
Patent number
US04240820

Reaction notes

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