Methyl chloroformate → HCID 10466372, compound

HRID 1199368Notes

Reaction equation

HRID 1199368 reaction equation
[CH2:1](N(CC)CC)C.[C:8]([C:11]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])(=O)[NH2:9].ClC(OC)=O>ClCCl>[C:8]([C:11]1[CH:19]=[C:18]([Cl:20])[C:17]([Cl:21])=[CH:16][C:12]=1[C:13]([O:15][CH3:1])=[O:14])#[N:9]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 10059905HCID 10059905, compound

Product 1

HCID 10466372HCID 10466372, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (25.4 mL, 0.182 mol) was added dropwise over a 20 minute period to a cold (0°-5° C.), stirred suspension of 2-carbamoyl-4,5-dichlorobenzoic acid (21.3 g, 91.0 mmol) in dichloromethane (110 mL). Methyl chloroformate (15.5 mL, 0.2 mol) was then added dropwise over a 30 minute period. The reaction mixture was then warmed to room temperature and stirred overnight. The solvents were removed and water (200 mL) was added. The water phase was filtered and the precipitate was washed with water and dried in vacuo to provide the product (20.5 g, 97%) as a tan solid, m.p. 120°-123° C.

Workup

  1. stirringstirred overnight
  2. customThe solvents were removed
  3. additionwater (200 mL) was added
  4. filtrationThe water phase was filtered
  5. washthe precipitate was washed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-5bb09cdbfbd34db88b1a82c9ad32dd31
Source dataset
uspto-grants-1990_02
Patent number
US04900739

Reaction notes

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