Hydrochloric Acid → 2-Bromo-5-chloro-N-methoxy-N-methylbenzamide

HRID 644950Notes

Reaction equation

HRID 644950 reaction equation
C(N(CC)C(C)C)(C)C.[Br:10][C:11]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:12]=1[C:13](O)=[O:14].[CH3:21][NH:22][O:23][CH3:24].Cl.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.O>[Br:10][C:11]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:12]=1[C:13]([N:22]([O:23][CH3:24])[CH3:21])=[O:14]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14232N,O-DimethylhydroxylamineHCID 81531DiisopropylethylamineHCID 890272-Bromo-5-chlorobenzoic 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 222365462-Bromo-5-chloro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N,N-diisopropylethylamine (1.10 mL, 6.36 mmol) was added to a stirred solution of 2-bromo-5-chlorobenzoic acid (0.500 g, 2.12 mmol), N,O-dimethylhydroxyl-amine.HCl (0.310 g, 3.18 mmol), and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoro-phosphate (1.21 g, 3.18 mmol) in N,N-dimethylformamide (8.5 mL) at ambient temperature. After 3 h, the reaction mixture was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, brine, dried (MgSO4) and concentrated in vacuo. Purification of the crude residue by flash chromatography on silica gel (gradient elution; 0-25% ethyl acetate/hexanes as eluent) gave the title compound as a colorless solid.

Workup

  1. customat ambient temperature
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic extracts were washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification of the crude residue by flash chromatography on silica gel (gradient elution; 0-25% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-6c8ab992014f401faa4c5f6464c700bc
Source dataset
uspto-grants-2010_04
Patent number
US07700778B2

Reaction notes

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