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

HRID 2388992Notes

Reaction equation

HRID 2388992 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:12]2[N:13]=[CH:14]C=CC=2N=N1.[Br:25][C:26]1[CH:27]=[CH:28][C:29]([I:35])=[C:30]([CH:34]=1)[C:31](O)=[O:32].CNC.C(N(C(C)C)CC)(C)C>CN(C)C=O.C(OCC)(=O)C>[Br:25][C:26]1[CH:27]=[CH:28][C:29]([I:35])=[C:30]([CH:34]=1)[C:31]([N:13]([CH3:14])[CH3:12])=[O:32]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 3029395-Bromo-2-iodobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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-efd9908d31564583ae1cd706577c2824
Source dataset
uspto-grants-2012_09
Patent number
US08268994B2

Reaction notes

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