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Bromoacetyl bromide → {2-[(2-Bromoacetyl)-(2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl ester

HRID 1694922
Notes
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Reaction equation

HRID 1694922 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[C:6]([O:10][C:11](=[O:25])[NH:12][C:13]([CH3:24])([CH3:23])[CH2:14][NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])([CH3:9])([CH3:8])[CH3:7].C(=O)(O)[O-].[Na+]>CN(C)C(=O)C>[C:6]([O:10][C:11](=[O:25])[NH:12][C:13]([CH3:24])([CH3:23])[CH2:14][N:15]([C:3](=[O:4])[CH2:2][Br:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH3:22])([CH3:9])([CH3:8])[CH3:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 66645699[1,1-Dimethyl-2-(2-methylphenylamino)ethyl]carbamic acid t-butyl ester

Product 1

HCID 66645910{2-[(2-Bromoacetyl)-(2-methylphenyl)amino]-1,1-dimethylethyl}carbamic acid t-butyl esterYield 93.3%

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent

Procedure

1.12 ml of bromoacetyl bromide (12.9 mmol) was added to a solution of 2.4 g of [1,1-dimethyl-2-(2-methylphenylamino)ethyl]carbamic acid t-butyl ester obtained in Example (51a) (8.62 mmol) in N,N-dimethylacetamide (85 ml) under ice-cooling, and the mixture was stirred at the same temperature for 10 minutes. A saturated sodium bicarbonate aqueous solution was added to the reaction mixture, followed by extraction with ethyl acetate. Then, the organic layer was washed with water and brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. Hexane was added to the residue, and the solid was collected by filtration to obtain 3.21 g of the title compound (yield: 93%).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThen, the organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationAfter filtration
  6. customthe solvent was evaporated under reduced pressure
  7. additionHexane was added to the residue
  8. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-00c3db40628a43f29a5540398d69111e
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08158790B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes