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

HRID 1095065Notes

Reaction equation

HRID 1095065 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-d782f58911c5426093582a1a5e849716
Source dataset
uspto-grants-2012_03
Patent number
US08133900B2

Reaction notes

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