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

HRID 1170763Notes

Reaction equation

HRID 1170763 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-8f6dd870cf754a6ea8895f95441b8e3e
Source dataset
uspto-grants-2010_11
Patent number
US07825246B2

Reaction notes

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