Chloroacetyl chloride → HCID 178476696, compound

HRID 1088658Notes

Reaction equation

HRID 1088658 reaction equation
[C:1]([O:4][N:5]=[C:6]([C:23]1[NH:24][C:25](=[NH:28])[S:26][CH:27]=1)[C:7]([O:9][CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:3])[CH3:2].C(N(CC)CC)C.[Cl:36][CH2:37][C:38](Cl)=[O:39].C(=O)([O-])O.[Na+]>CN(C)C=O.O>[C:1]([O:4][N:5]=[C:6]([C:23]1[NH:24][C:25](=[N:28][C:38](=[O:39])[CH2:37][Cl:36])[S:26][CH:27]=1)[C:7]([O:9][CH:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6577Chloroacetyl chloride2×HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178476697HCID 178476697, compound

Product 1

HCID 178476696HCID 178476696, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 100 ml of N,N-dimethylformamide there were suspended 19.7 g of benzhydryl 2-acetoxyimino-2-(2-imino-4-thiazolin-4-yl)acetate, followed by the addition of 6.02 g of triethylamine. Under ice-cooling and stirring, 4.98 ml of chloroacetyl chloride were added dropwise. The mixture was further stirred at that temperature for 10 minutes and, then, at room temperature for 20 minutes. Thereafter, 1.50 ml of chloroacetyl chloride was added dropwise and the mixture were stirred for 20 minutes. The reaction mixture was poured into a solution of 4.4 g of sodium hydrogen carbonate in 200 ml of water and extracted with 500 ml of ethyl acetate in three installments. The ethyl acetate layers were pooled, washed twice with 100 ml of a 1e aqueous solution of sodium hydrogen carbonate and further washed with a saturated aqueous solution of sodium chloride. The drying with magnesium sulfate and the decolorization with activated carbon were concurrently carried out and, after filtering, the solvent was distilled off. To the residue there were added 20 ml of ethyl acetate and the mixture was allowed to stand. The resultant crystals were recovered by filtration and dried. By the above procedure there were obtained 12.7 g of benzhydryl 2-acetoxyimino-2-(2-chloroacetylimino-4-thiazolin-4-yl)acetate (syn-isomer). This product contained a small amount of the anti-isomer, which was removed by the following procedure.

Workup

  1. temperatureUnder ice-cooling
  2. stirringThe mixture was further stirred at that temperature for 10 minutes
  3. stirringthe mixture were stirred for 20 minutes
  4. extractionextracted with 500 ml of ethyl acetate in three installments
  5. washwashed twice with 100 ml of a 1e aqueous solution of sodium hydrogen carbonate
  6. washfurther washed with a saturated aqueous solution of sodium chloride
  7. filtrationafter filtering
  8. distillationthe solvent was distilled off
  9. additionTo the residue there were added 20 ml of ethyl acetate
  10. filtrationThe resultant crystals were recovered by filtration
  11. customdried

Sources & evidence

ORD record
ord-18f49a9b925c44929772bd595d4829bb
Source dataset
uspto-grants-1990_10
Patent number
US04963542

Reaction notes

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