Diethyl Ether → HCID 22010754, compound

HRID 323177Notes

Reaction equation

HRID 323177 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:47]=[CH:46][C:20]([C:21]([N:23]([CH3:45])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[S:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([N:38]4[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]4)=[O:37])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:56])C=1.C(OCC)C>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:47]=[CH:46][C:20]([C:21]([N:23]([CH3:45])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[S:30]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][C:36]([N:38]4[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH2:43]4)=[O:37])=[O:56])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 70297m-Chloroperbenzoic acidHCID 22010883HCID 22010883, compound

Product 1

HCID 22010754HCID 22010754, compoundYield 82.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-ylthio]phenyl]benzamide (500 mg) and m-chloroperbenzoic acid (133 mg) in dichloromethane (20 ml) was stirred in an ice bath for 2 hours and the solution was washed successively with saturated aqueous sodium hydrogen carbonate, water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give a syrup. The crude product was solidified with diethyl ether to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[5-(4-methylpiperazin-1-yl)carbonylpent-1-ylsulfinyl]phenyl]benzamide (423 mg) as a white powder.

Workup

  1. washthe solution was washed successively with saturated aqueous sodium hydrogen carbonate, water and brine
  2. dry with materialThe organic solution was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customto give a syrup

Sources & evidence

ORD record
ord-7666be9738164f83bfb26653a9e13af4
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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