Phosgene → HCID 12767621, compound

HRID 903810Notes

Reaction equation

HRID 903810 reaction equation
C(N(CC)CC)C.[CH3:8][NH:9][C:10](=[O:25])[C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:20])[CH3:19])=[C:13]([O:21][C:22](=[O:24])[CH3:23])[CH:12]=1.C[Si](Cl)(C)C.[C:31]([Cl:34])(Cl)=[O:32]>ClCCl>[C:22]([O:21][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][C:14]=1[O:17][C:18](=[O:20])[CH3:19])[C:10]([N:9]([CH3:8])[C:31]([Cl:34])=[O:32])=[O:25])(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 12767620HCID 12767620, compound

Product 1

HCID 12767621HCID 12767621, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of triethylamine (6.04 g) in anhydrous dichloromethane (20 ml) was added dropwise at room temperature to a solution of N-methyl-3,4-diacetoxybenzamide (15.0 g) and trimethylsilyl chloride (6.49 g) in anhydrous dichloromethane (70 ml). After the mixture was refluxed for 20 minutes, a solution of phosgene (42 ml) in anhydrous dichloromethane (82 ml) was added to the mixture at a temperature of from -5° to 5° C. by allowing its temperature to gradually rise to room temperature. Excess phosgene and the solvent used were evaporated to dryness under reduced pressure to give crude N-(3,4-diacetoxybenzoyl)-N-methylcarbamoyl chloride. The product was dissolved in cold anhydrous dichloromethane (50 ml) and, after removing insoluble substances by filtration, made available for the subsequent reaction.

Workup

  1. temperatureAfter the mixture was refluxed for 20 minutes
  2. customto gradually rise to room temperature
  3. customExcess phosgene and the solvent used were evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f582bfd446e243d38a745ffd1d94ba44
Source dataset
uspto-grants-1980_10
Patent number
US04229348

Reaction notes

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