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

HRID 2415551Notes

Reaction equation

HRID 2415551 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 (3-1) (0.500 g, 2.12 mmol), N,O-dimethylhydroxylamine.HCl (0.310 g, 3.18 mmol), and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (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 3-2 (0.56 g) 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-76abed9d545f47c09e0dc7106a76daed
Source dataset
uspto-grants-2004_11
Patent number
US06818658B2

Reaction notes

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