Water → HCID 86644409, compound

HRID 2194675Notes

Reaction equation

HRID 2194675 reaction equation
[CH3:1][N:2]([CH2:10][C:11]1[S:12][CH:13]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:15]=1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].[Br:22]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:22][C:13]1[S:12][C:11]([CH2:10][N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7])=[CH:15][C:14]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 68412910HCID 68412910, compound

Product 1

HCID 86644409HCID 86644409, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl methyl[(4-phenyl-2-thienyl)methyl]carbamate (4.77 g) in N,N-dimethylformamide (30 mL) was added N-bromosuccinimide (2.83 g) at room temperature and the mixture was stirred for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=99:1→19:1) to give the title compound as a pale-yellow oil (yield 4.1 g, yield of 2 steps 67%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=99:1→19:1)

Sources & evidence

ORD record
ord-ca5d35738dcc46f089bed00952085796
Source dataset
uspto-grants-2012_12
Patent number
US08334301B2

Reaction notes

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