Methyl chloroformate → Methyl 2-(4-methoxyphenylthio)ethylcarbamate

HRID 1917062Notes

Reaction equation

HRID 1917062 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][NH2:13])=[CH:6][CH:5]=1.Cl[C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:11][CH2:12][NH:13][C:15](=[O:16])[O:17][CH3:18])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 122619332-(4-Methoxyphenylthio)ethanamine hydrochloride

Product 1

HCID 57864658Methyl 2-(4-methoxyphenylthio)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 1-HCl (0.466 g) in CH2Cl2 (20 mL) cooled to ˜0° C. was added methyl chloroformate (1.1 eq.) and triethylamine (2.5 eq.). The reaction mixture was stirred for 2 hours at 0° C. and washed with 1N HCl, and sat. NaHCO3. The solvents were removed by evaporation under reduced pressure to give product 7 as white solid with a yield of 480 mg, 98%.

Workup

  1. washwashed with 1N HCl, and sat. NaHCO3
  2. customThe solvents were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-8750feda5c6a4ea29967aef840d837b7
Source dataset
uspto-grants-2013_12
Patent number
US08618282B2

Reaction notes

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