Pyridine → alpha-Acetoxy-[2-(beta,beta,beta-trichloroethoxycarbonyl)aminothiazol-4-yl]acetonitrile

HRID 866437Notes

Reaction equation

HRID 866437 reaction equation
[OH:1][CH:2]([C:5]1[N:6]=[C:7]([NH:10][C:11]([O:13][CH2:14][C:15]([Cl:18])([Cl:17])[Cl:16])=[O:12])[S:8][CH:9]=1)[C:3]#[N:4].N1C=CC=CC=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].CCOCC>O>[C:25]([O:1][CH:2]([C:5]1[N:6]=[C:7]([NH:10][C:11]([O:13][CH2:14][C:15]([Cl:17])([Cl:18])[Cl:16])=[O:12])[S:8][CH:9]=1)[C:3]#[N:4])(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 15137534alpha-Hydroxy[2-(beta,beta,beta-trichloroethoxycarbonyl)aminothiazol-4-yl]acetonitrile

Product 1

HCID 15137535alpha-Acetoxy-[2-(beta,beta,beta-trichloroethoxycarbonyl)aminothiazol-4-yl]acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 1.10 g. of α-hydroxy-[2-(β,β,β-trichloroethoxycarbonyl)aminothiazol-4-yl)acetonitrile in 1 ml. of pyridine is added 2.5 ml. of acetic anhydride under ice-cooling and the mixture is stirred for 1 hour. To the mixture is added ether and water and the organic layer is washed with aq. NaHCO3 and further water in this order. Evaporation of ether gives α-acetoxy-[2-(β,β,β-trichloroethoxycarbonyl)aminothiazol-4-yl]acetonitrile. 1.3 g. NMR(ppm, 100 MHz, CDCl3): 2.20(3H,s,COCH3), 5.00(2H,s, Cl3CCH2 --), 6.60(1H,s, >CHCN), 7.30(1H,s,5-H).

Workup

  1. washthe organic layer is washed with aq. NaHCO3 and further water in this order
  2. customEvaporation of ether

Sources & evidence

ORD record
ord-91862377e0a54ef6b28c82a1b079c73c
Source dataset
uspto-grants-1978_07
Patent number
US04098888

Reaction notes

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