Chloride → HCID 53909736, compound

HRID 850178Notes

Reaction equation

HRID 850178 reaction equation
[CH3:1][C:2]1[C:7]([N:8]([CH3:27])[C:9](=[O:26])[CH2:10][NH:11][C:12](=[O:25])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:24])[NH:22][CH3:23])=[CH:17][CH:16]=2)=[CH:6][CH:5]=[C:4]([CH3:28])[C:3]=1[CH2:29]O.[Cl-:31].O>CN(C)C=O>[CH3:1][C:2]1[C:7]([N:8]([C:9](=[O:26])[CH2:10][NH:11][C:12](=[O:25])[CH:13]=[CH:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:24])[NH:22][CH3:23])=[CH:17][CH:16]=2)[CH3:27])=[CH:6][CH:5]=[C:4]([CH3:28])[C:3]=1[CH2:29][Cl:31]

Participants

5

Reactant 3

HCID 312ChlorideHCID 962WaterHCID 54456548HCID 54456548, compound

Product 1

HCID 53909736HCID 53909736, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6-dimethyl-1-hydroxymethyl-3-[N-methyl-N-[4-(methylcarbamoyl)cinnamoylglycyl]amino]benzene (2.00 g) in N,N-dimethylformamide (100 ml) was added mezhanesulfonyl chloride (784 mg) under ice-cooling, and the mixture was stirred for 2 hours at the same temperature and overnight at ambient temperature. To the mixture was added water and extracted with chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was pulverized with diethyl ether to give 2,6-dimethyl-3-[N-[4-(methylcarbamoyl)-cinnamoylglycyl]-N-methylamino]benzyl chloride (2.00 g) as white powder.

Workup

  1. temperaturecooling
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ba867618aff541059c4bed2dcccdb6a3
Source dataset
uspto-grants-2000_01
Patent number
US06015818

Reaction notes

Loading…