Ethyl chloroformate → HCID 19891922, compound

HRID 893295Notes

Reaction equation

HRID 893295 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6]N(C)C)=[C:4]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:3]=1.[Cl:22]C(OCC)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][Cl:22])=[C:4]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 19891926HCID 19891926, compound

Product 1

HCID 19891922HCID 19891922, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-chloro-2-(4-methoxybenzylthio)-N,N-dimethylbenzylamine (D19) (2.49 g, 7.7 mmol) in dry toluene (80 ml) was cooled in ice whilst ethyl chloroformate (0.9 ml, 9.4 mmol) was added dropwise. A solid slowly separated, and after 1 h at 0-5° C. the mixture was heated under reflux for 2 h. The solvent was removed in vacuo, then the residue was repeatedly dissolved in toluene and evaporated to dryness (3 times) to give the title compound as a light brown oil (2.36 g, 98%).

Workup

  1. additionwas added dropwise
  2. customA solid slowly separated
  3. temperatureunder reflux for 2 h
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue was repeatedly dissolved in toluene
  6. customevaporated to dryness (3 times)

Sources & evidence

ORD record
ord-5377880e088f4a5b8d8bb526e9049dfe
Source dataset
uspto-grants-1992_06
Patent number
US05124322

Reaction notes

Loading…