Phosgene → HCID 12767621, compound

HRID 1065074Notes

Reaction equation

HRID 1065074 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 dried 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 dried dichloromethane (70 ml). After the mixture was refluxed for 30 minutes a solution (82 ml) of phosgene (42 ml) in dried dichloromethane was added to the mixture at a temperature of from -5° to 5° C. followed by allowing its temperature to gradually rise to room temperature. Excess phosgene and the solvent used were removed by evaporation under reduced pressure to give crude N-(3,4-diacetoxybenzoyl)-N-methylcarbamoyl chloride. The product was dissolved in cold dried dichloromethane (50 ml) and, after removing insoluble substances by filtration, made available for the subsequent reaction.

Workup

  1. additionwas added to the mixture at a temperature of from -5° to 5° C.
  2. customto gradually rise to room temperature
  3. customExcess phosgene and the solvent used were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-7be1e272658247899a7bb376c4f26e78
Source dataset
uspto-grants-1982_05
Patent number
US04328224

Reaction notes

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