Water → HCID 58941361, compound

HRID 747618Notes

Reaction equation

HRID 747618 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([CH:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])O)[CH:3]=1.[H-].[Na+].Br[CH2:34][C:35]([NH2:37])=[O:36].O>CN(C=O)C>[Cl:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:22][C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][C:5]=1[N:8]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)(=[O:10])=[O:11])[CH2:34][C:35]([NH2:37])=[O:36]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 68567562HCID 68567562, compound

Product 1

HCID 58941361HCID 58941361, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 0.47 g of N-{4-methyl-2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamide dissolved in 5.7 ml of DMF is added, at 0° C., 0.048 g of sodium hydride. After 1 hour at this temperature, 0.166 g of 2-bromoacetamide is introduced and the mixture is left for 18 hours at room temperature. The medium is poured into water and then extracted with ethyl acetate. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with a 90/10 (v/v) cyclohexane/ethyl acetate mixture to give 0.4 g of the expected product.

Workup

  1. additionis added, at 0° C.
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with a 90/10 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-65276b83456c4c59bf3b09de5f503bab
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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