Ethyl chloroformate → HCID 19891914, compound

HRID 893294Notes

Reaction equation

HRID 893294 reaction equation
[Cl:1]C(OCC)=O.[CH2:7]([S:14][C:15]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:16]=1[CH2:17]N(C)C)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CCOCC>[CH2:7]([S:14][C:15]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[CH:21][C:16]=1[CH2:17][Cl:1])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 19891909HCID 19891909, compound

Product 1

HCID 19891914HCID 19891914, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Ethyl chloroformate (0.6 ml, 6.2 mmol) was added dropwise to an ice-cooled solution of 2-benzylthio-3-methoxy-N,N-dimethyl benzylamine (1.5 g, 5.2 mmol) in dry ether (40 ml). The mixture was stirred at room temperature for 2 h. The solvent was evaporated in vacuo, and the residual solid was extracted several times with hexane. The extracts were evaporated to leave the title compound as a solid (1.29 g, 89%), mp 54°-55C. (Found: C,64.67; H,5.50; Cl,12.99. C15H15ClOS requires C,64.62; H,5.42; Cl,12.72%).

Workup

  1. customThe solvent was evaporated in vacuo
  2. extractionthe residual solid was extracted several times with hexane
  3. customThe extracts were evaporated

Sources & evidence

ORD record
ord-23a97ebf0596430c921bc0678cbbd141
Source dataset
uspto-grants-1992_06
Patent number
US05124322

Reaction notes

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