Thionyl Chloride → 2-Methyl-6-methoxycarbonylaminobenzyl chloride

HRID 2073797Notes

Reaction equation

HRID 2073797 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([O:13][CH3:14])=[O:12])[C:3]=1[CH2:4]O.S(Cl)([Cl:17])=O>C(Cl)Cl>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([O:13][CH3:14])=[O:12])[C:3]=1[CH2:4][Cl:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14368454Methyl (2-(hydroxymethyl)-3-methylphenyl)carbamate

Product 1

HCID 143684802-Methyl-6-methoxycarbonylaminobenzyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-methyl-6-methoxycarbonylaminobenzyl alcohol (29.19 g) in methylene chloride (290 ml) was added dropwise thionyl chloride (11.46 ml) at room temperature and the resultant mixture was stirred for 2 hours. After the solvent was evaporated in vacuo, n-hexane was added to the residue to give precipitates. The precipitates were collected by filtration and dried to give 2-methyl-6-methoxycarbonylaminobenzyl chloride (28.26 g).

Workup

  1. customAfter the solvent was evaporated in vacuo, n-hexane
  2. additionwas added to the residue
  3. customto give
  4. customprecipitates
  5. filtrationThe precipitates were collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-eed79d116bc74f719df6ac07aac571a7
Source dataset
uspto-grants-1990_04
Patent number
US04920129

Reaction notes

Loading…