Dimethylamine → 5-bromo-2-iodo-N,N-dimethylbenzamide

HRID 1865655Notes

Reaction equation

HRID 1865655 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:12][NH:13][CH3:14].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([I:11])=[C:6]([CH:10]=1)[C:7]([N:13]([CH3:14])[CH3:12])=[O:8]

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 3029395-Bromo-2-iodobenzoic acid

Product 1

HCID 524394945-bromo-2-iodo-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N-tetramethyluronium hexafluorophosphate (1.16 g, 3.06 mmol) was added to a solution of 5-bromo-2-iodo-benzoic acid (1.00 g, 3.06 mmol), dimethyl amine (2 M in THF, 3.06 ml, 3.06 mmol) and di-iso-propyl ethyl amine (1.59 ml, 9.18 mmol) in N,N-Dimethylformamide (12 ml). The reaction was stirred at room temperature overnight. Ethyl acetate was added and the mixture was washed with water, the organic layer was dried over magnesium sulfate and evaporated. The residue was purified by silica gel chromatography to yield 5-bromo-2-iodo-N,N-dimethyl-benzamide as a white solid. (0.96 g, 90%). MS: m/z 328.1 (M+H+).

Workup

  1. washthe mixture was washed with water
  2. dry with materialthe organic layer was dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-35a3429b393a4dac990c3c9ad396e214
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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