Phosgene → HCID 85868104, compound

HRID 1182113Notes

Reaction equation

HRID 1182113 reaction equation
[C:1]([Cl:4])(Cl)=[O:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9](NC)[CH:10]=[C:11]([O:13][CH3:14])[CH:12]=1.[CH2:17]([N:19](CC)CC)C>C1(C)C=CC=CC=1.ClCCl>[CH3:14][O:13][C:11]1[CH:10]=[C:9]([CH2:17][NH:19][C:1]([Cl:4])=[O:2])[CH:8]=[C:7]([O:6][CH3:5])[CH:12]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 145235363,5-Dimethoxy-N-methylbenzenamine

Product 1

HCID 85868104HCID 85868104, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of phosgene (11.6 mmol) in toluene (6 ml) is diluted with dichloromethane (15 ml) and cooled to 0° C. To this is added a solution of (3,5-Dimethoxy-phenyl)-methyl-amine (1.67 g, 10 mmol) and triethylamine (1.78 ml, 14.0 mmol) in dichloromethane (5 ml) slowly over 30 minutes, and the reaction mixture allowed to warm to ambient temperature with stirring over 2 hours. After stirring at ambient temperature for a further 2 hours, the reaction mixture is partitioned between ether and 1M hydrochloric acid solution. The ether phase is washed with brine, dried over magnesium sulphate and evaporated to afford (3,5-Dimethoxy-phenyl)methyl-carbamoyl chloride as a white solid.

Workup

  1. temperatureto warm to ambient temperature
  2. stirringAfter stirring at ambient temperature for a further 2 hours
  3. customthe reaction mixture is partitioned between ether and 1M hydrochloric acid solution
  4. washThe ether phase is washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-383c105e13fd49cda3432c6f712c77c1
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

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