Ethyl (chloroformyl)acetate → HCID 13125118, compound

HRID 1758665Notes

Reaction equation

HRID 1758665 reaction equation
[C:1]([N:10]([CH2:12][C:13]([NH2:15])=[S:14])[CH3:11])([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:2].[CH:16]([CH:18](Cl)[C:19]([O:21][CH2:22][CH3:23])=[O:20])=O>ClCCCl>[C:19]([C:18]1[S:14][C:13]([CH2:12][N:10]([C:1]([O:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:2])[CH3:11])=[N:15][CH:16]=1)([O:21][CH2:22][CH3:23])=[O:20]

Participants

4

Reactant 2

HCID 118030Ethyl (chloroformyl)acetate2×HCID 13102903HCID 13102903, compound

Product 1

HCID 13125118HCID 13125118, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

(N-Carbophenoxy-N-methylamino)thioacetamide (46.7 g; 0.21 moles) was combined with ethyl α-formylchloroacetate (30.0 g; 0.20 moles) in 270 ml of 1,2-dichloroethane and heated to reflux temperature for 2 hours. An additional amount of ethyl α-formylchloroacetate (3.0 g; 0.02 moles) was added and heating was continued for 1.5 hours. The reaction mixture was extracted with two 300 ml portions of cold 5% aqueous sodium carbonate, then washed with two 300 ml portions of water and dried over Na2SO4. Evaporation gave the product as an oil which slowly crystallized. Recrystallization from 2-propanol yielded 26 g of the title compound, mp 81°-83°.

Workup

  1. temperatureheated
  2. temperatureto reflux temperature for 2 hours
  3. temperatureheating
  4. extractionThe reaction mixture was extracted with two 300 ml portions of cold 5% aqueous sodium carbonate
  5. washwashed with two 300 ml portions of water
  6. dry with materialdried over Na2SO4
  7. customEvaporation

Sources & evidence

ORD record
ord-0892a3e6d9454614b8513df2ffc05f5b
Source dataset
uspto-grants-1983_02
Patent number
US04374248

Reaction notes

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