Chloroform → HCID 54392061, compound

HRID 2287467Notes

Reaction equation

HRID 2287467 reaction equation
[Cl:1][C:2]1[C:7]([N:8]([CH3:28])[C:9](=[O:27])[CH2:10][NH:11][C:12](=[O:26])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[CH:17][CH:16]=2)=[CH:6][CH:5]=[C:4]([Cl:29])[C:3]=1[CH2:30][OH:31].C(N(CC)CC)C.[S:39](Cl)([CH3:42])(=[O:41])=[O:40].C(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[C:7]([N:8]([CH3:28])[C:9](=[O:27])[CH2:10][NH:11][C:12](=[O:26])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])=[CH:17][CH:16]=2)=[CH:6][CH:5]=[C:4]([Cl:29])[C:3]=1[CH2:30][O:31][S:39]([CH3:42])(=[O:41])=[O:40]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54199430HCID 54199430, compound

Product 1

HCID 54392061HCID 54392061, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2,6-dichloro-1-hydroxymethyl-3-[N-methyl-N-[4-(dimethylcarbamoyl)cinnamoylglycyl]amino]benzene (300 mg) and triethylamine (78.5 mg) in dichloromethane (3 ml) was dropwise added mesyl chloride (81.4 mg) under ice-cooling, and the mixture was stirred for 10 minutes at the same temperature and for 30 minutes at ambient temperature. Chloroform was added thereto, and the mixture was washed with saturated sodium bicarbonate solution, water and brine, dried over magnesium sulfate and evaporated in vacuo to give 2,6-dichloro-1-methanesulfonyloxymethyl-3-[N-methyl-N-[4-(dimethylcarbamoyl)cinnamoylglycyl]amino]benzene (330 mg) as colorless amorphous.

Workup

  1. temperaturecooling
  2. washthe mixture was washed with saturated sodium bicarbonate solution, water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-47467480206948b1b93c029e6cc1d452
Source dataset
uspto-grants-2000_07
Patent number
US06083959

Reaction notes

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