Isopropylamine → 3-bromo-N-isopropylbenzamide

HRID 1097119Notes

Reaction equation

HRID 1097119 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[CH:11]([NH2:14])([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:14][CH:11]([CH3:13])[CH3:12])=[O:6]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 74377Benzoyl chloride, 3-bromo-

Product 1

HCID 6693113-bromo-N-isopropylbenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-benzoyl chloride (0.83 g, 3.8 mmol) in DCM (40 mL) was chilled to zero degrees and treated with isopropylamine (0.96 mL, 11.32 mmol). Reaction was allowed to come to room temperature and stir for 24 h. Mixture was then poured onto water and washed once. Organic phase then washed with brine, dried over sodium sulfate, filtered and evaporated to white solids (0.6 g, 66%).

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 white solids (0.6 g, 66%)

Sources & evidence

ORD record
ord-67fc43a1a67a496da2f900eaf8e1e116
Source dataset
uspto-grants-2012_03
Patent number
US08138199B2

Reaction notes

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