Chloroacetonitrile → HCID 53783600, compound

HRID 255750Notes

Reaction equation

HRID 255750 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:38][OH:39])[C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:31]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl[CH2:41][C:42]#[N:43]>CN(C)C=O>[C:7]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:38][O:39][CH2:41][C:42]#[N:43])[C:33]([O:35][CH2:36][CH3:37])=[O:34])[N:31]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 6802348Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate

Product 1

HCID 53783600HCID 53783600, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (4.84 g.) was added to a stirred solution of ethyl 2-(2-tritylaminothiazol-4-yl)-2-hydroxyiminoacetate (syn isomer, 10 g.) in N,N-dimethylformamide (22.0 ml.). Chloracetonitrile (2.64 g.) was added dropwise to the solution under nitrogen atmosphere and stirred at room temperature for 5 hours. After removing the insoluble substance from the resultant mixture by filtration, water (300 ml.) was added to the filtrate and extracted with ethyl acetate (300 ml.). The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, treated with activated charcoal and concentrated in vacuo. The residue was pulverized with a mixture of n-hexane, ethyl acetate and acetone (4:4:1) and then the precipitates were collected by filtration and washed with n-hexane to give ethyl 2-(2-tritylaminothiazol-4-yl)-2-cyanomethoxyiminoacetate (syn isomer, 9.58 g.).

Workup

  1. customAfter removing the insoluble substance from the resultant mixture
  2. filtrationby filtration, water (300 ml.)
  3. additionwas added to the filtrate
  4. extractionextracted with ethyl acetate (300 ml.)
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. additiontreated with activated charcoal
  8. concentrationconcentrated in vacuo
  9. additionThe residue was pulverized with a mixture of n-hexane, ethyl acetate and acetone (4:4:1)
  10. filtrationthe precipitates were collected by filtration
  11. washwashed with n-hexane

Sources & evidence

ORD record
ord-f6b151c25b1941f2a29b9923d0d28c7c
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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