Bromoacetyl chloride → HCID 14292484, compound

HRID 1054031Notes

Reaction equation

HRID 1054031 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)(O)[O-].[Na+].[Br:19][CH2:20][C:21](Cl)=[O:22]>CN(C)C=O>[Br:19][CH2:20][C:21]([N:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:22]

Participants

5

Reactant 3

HCID 89602Bromoacetyl chlorideHCID 516892Sodium BicarbonateHCID 1133193HCID 1133193, compound

Product 1

HCID 14292484HCID 14292484, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. stirring suspension of the N-(thiophen-2-ylmethyl)aniline (3.51 g, 18.53 mmol) and sodium bicarbonate (1.71 g, 20.38 mmol) in dimethylformamide (15.0 mL), it was added bromoacetyl chloride (1.54 mL, 18.53 mmol). The ice bath was removed and the flask was attached to a bubbler to allow gas evolution and expansion. The reaction was stirred overnight at room temp. Most of the volatiles were evaporated in vacuo, then the residue was taken up in dichloromethane and was washed with water first and then brine. The resulting organic layer was dried over MgSO4(s) and concentrated. The obtained crude was absorbed under vacuum on Florisil with the aid of DCM (dry load). The obtained dispersion was purified by column chromatography (Biotage system, hex:EtOAc 1-20% gradient over 30 CV, 40 g Silicycle silica column) The collected fractions were evaporated to afford 4.51 g of 2-bromo-N-phenyl-N-(thiophen-2-ylmethyl)acetamide (14.55 mmol; 78%), which was judged more than 97% pure by 1H-NMR analysis.

Workup

  1. customThe ice bath was removed
  2. stirringThe reaction was stirred overnight at room temp
  3. customMost of the volatiles were evaporated in vacuo
  4. washwas washed with water first
  5. dry with materialThe resulting organic layer was dried over MgSO4(s)
  6. concentrationconcentrated
  7. customThe obtained crude
  8. customwas absorbed under vacuum on Florisil with the aid of DCM (dry load)
  9. customThe obtained dispersion was purified by column chromatography (Biotage system, hex:EtOAc 1-20% gradient over 30 CV, 40 g Silicycle silica column) The collected fractions
  10. customwere evaporated

Sources & evidence

ORD record
ord-533e2d6eeef949d8a3dc70e82198f8ce
Source dataset
uspto-grants-2016_07
Patent number
US09394287B2

Reaction notes

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