Chloroacetonitrile → ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(cyanomethoxyimino)acetate

HRID 1195060Notes

Reaction equation

HRID 1195060 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[OH:14])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22][C:23]#[N:24]>CN(C)C=O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:22][C:23]#[N:24])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Product 1

HCID 88630612ethyl (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(cyanomethoxyimino)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

54 g of ethyl 2-(2-amino-4-thiazolyl)-2-(Z)-hydroxyimino-acetate are dissolved in 500 ml of dimethylformamide. After the addition of 138 g of potassium carbonate, there are added dropwise within 1 hour 47 ml of chloroacetonitrile and the mixture is then stirred at room temperature for 20 hours. The dark solution obtained is poured into ice-water and extracted with ethyl acetate. The organic phase is washed with water, treated with active carbon, dried over magnesium sulphate and concentrated. After recrystallization from toluene, there are obtained 38 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-(cyanomethoxy)imino]-acetate of melting point 167°-168° C.

Workup

  1. customThe dark solution obtained
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. additiontreated with active carbon
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated
  7. customAfter recrystallization from toluene, there

Sources & evidence

ORD record
ord-e5e3966c4af540059c66a4dc0610ab57
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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