Tert-Butylamine → N-t-Butyl 3-bromobenzamide

HRID 491228Notes

Reaction equation

HRID 491228 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11]([NH2:15])([CH3:14])([CH3:13])[CH3:12]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH:15][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 603211N-t-Butyl 3-bromobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-benzoyl chloride (0.83 g, 3.8 mmol) in DCM (10 mL) was chilled to zero degrees and treated with tert-butylamine (1.2 mL, 11.3 mmol). Reaction was allowed to come to room temperature and stir for 4 h. Mixture was then poured onto water and washed once. Organic phase then washed with brine, dried over sodium sulfate, filtered and evaporated to amber oil (0.9 g, 94%).

Workup

  1. customReaction
  2. customto come to room temperature
  3. additionMixture was then poured onto water
  4. washwashed once
  5. washOrganic phase then washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated to amber oil (0.9 g, 94%)

Sources & evidence

ORD record
ord-5d1e6cbf2a7b481bb2e3250b5c55136e
Source dataset
uspto-grants-2009_05
Patent number
US07528143B2

Reaction notes

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