Water → HCID 69414610, compound

HRID 1351306Notes

Reaction equation

HRID 1351306 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[S:9][CH:10]=[CH:11][C:12]=1[S:13](=[O:27])(=[O:26])[N:14]([CH2:16][CH:17]([C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[OH:18])[CH3:15])([CH3:4])([CH3:3])[CH3:2].[Br:29]N1C(=O)CCC1=O.O>CN(C)C=O>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1[S:9][C:10]([Br:29])=[CH:11][C:12]=1[S:13](=[O:27])(=[O:26])[N:14]([CH2:16][CH:17]([C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)[OH:18])[CH3:15])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 69413728HCID 69413728, compound

Product 1

HCID 69414610HCID 69414610, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3-{[2-(4-fluorophenyl)-2-hydroxy-ethyl]-methyl-sulfamoyl}-thiophene-2-yl) carbamic acid t-butyl ester (the compound of Preparation Example 96) (6 g) in N,N-dimethylformamide (50 mL) was added N-bromosuccinimide (2.6 g) in small amounts on an ice bath. After stirring at room temperature for 1 hour, water was added, the solution was extracted with ethyl acetate. After the organic layer was washed with water, an aqueous solution of sodium bicarbonate and saturated sodium chloride water, and was dried with anhydrous magnesium sulfate. The extract was purified by passing through a column of NH silica gel, and the title compound (6.6 g) was obtained as a colorless candy-like substance.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washAfter the organic layer was washed with water
  3. dry with materialan aqueous solution of sodium bicarbonate and saturated sodium chloride water, and was dried with anhydrous magnesium sulfate
  4. customThe extract was purified

Sources & evidence

ORD record
ord-1cd3384ce8b544caabc69940de9a20b2
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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