Methyl chloroacetate → HCID 20551621, compound

HRID 1154901Notes

Reaction equation

HRID 1154901 reaction equation
Cl[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH2:7]([S:14][C:15](=S)[NH:16][NH2:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O1CC[CH2:21][CH2:20]1>>[CH2:7]([S:14][C:15]1[C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:20]([CH3:21])[NH:17][N:16]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 3

HCID 7295Methyl chloroacetateHCID 8028TetrahydrofuranHCID 4694188Benzyl hydrazinecarbodithioate

Product 1

HCID 20551621HCID 20551621, compound

Procedure

At room temperature, 47 g of methyl 2-chloroacetate is added to a solution of 55 g of dithiocarbazic acid-S-benzyl ester in 250 ml of tetrahydrofuran. After stirring for 16 hours at room temperature, the precipitated solids mixture is filtered and washed with diethyl ether, and the residue is stirred into 200 ml of 12% strength ammonia solution. The product has the sulfur removed from it by extraction with methylene chloride. After drying over sodium sulfate, the methylene chloride is distilled off and the solid which remains is recrystallized from ethyl acetate. Melting point: 109°-110° C.

Workup

  1. filtrationthe precipitated solids mixture is filtered
  2. washwashed with diethyl ether
  3. stirringthe residue is stirred into 200 ml of 12% strength ammonia solution
  4. customremoved from it by extraction with methylene chloride
  5. dry with materialAfter drying over sodium sulfate
  6. distillationthe methylene chloride is distilled off
  7. customthe solid which remains is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5a0da81ee403415eabbf863c259b6017
Source dataset
uspto-grants-1981_11
Patent number
US04298749

Reaction notes

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