Dimethylformamide → HCID 21914727, compound

HRID 2117917Notes

Reaction equation

HRID 2117917 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:27][C:28](=[O:30])[CH3:29])[S:14][C:15]=2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:5][CH:4]=1.C(Cl)[Cl:32].CN(C=O)C.CS(Cl)(=O)=O>O.CCN(CC)CC>[Cl:32][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:27][C:28](=[O:30])[CH3:29])[S:14][C:15]=2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 31297Methanesulfonyl chlorideHCID 21915121HCID 21915121, compound

Product 1

HCID 21914727HCID 21914727, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

N-{4-{2-[4-(Hydroxymethyl)phenyl]ethyl}-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (539.5 mg), CH2Cl2 (5 ml) and DMF (5 ml) were combined under N2 atmosphere. Then, Et3N (0.211 ml) and MsCl (0.108 ml) were added to the suspension at 0° C. The reaction mixture was stirred at r.t. for 3.5 hours. The reaction mixture was poured into water, and extracted with CHCl3. The organic layer was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residual solid was washed with ethyl ether to give N-{4-{2-[4-(chloromethyl)phenyl]ethyl}-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (537.5 mg) as an off-white solid.

Workup

  1. extractionextracted with CHCl3
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe residual solid was washed with ethyl ether

Sources & evidence

ORD record
ord-aa4c5c1dc77a48aca5b49f71846ffc18
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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