Diisopropylethylamine → 4-bromo-2-chloro-N-methoxy-N-methylbenzamide

HRID 40275

Reaction equation

HRID 40275 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([Cl:11])[CH:3]=1.CCN(C(C)C)C(C)C.CN([C:24]([O:28][N:29]1N=NC2C=CC=N[C:30]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:29]([O:28][CH3:24])[CH3:30])=[O:7])=[C:4]([Cl:11])[CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1088294-Bromo-2-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 598430764-bromo-2-chloro-N-methoxy-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 4-bromo-2-chlorobenzoic acid (3.45 g, 15 mmol) and DIEA (7.7 ml, 44 mmol) in DMF (30 mL) was added HATU (6.1 g, 16 mmol) at 23° C. under nitrogen. Darkened suspension stirred for 1 h, then added n,o-dimethylhydroxylamine hydrochloride (2.1 g, 22 mmol). Solution stirred overnight at 23° C. Reaction then partitioned between 2.5% NaHCO3 (250 mL) and diethyl ether (100 mL). Aqueous further extracted with ether (2×50 mL). Combined ethereal extracts dried over MgSO4, then concentrated an amber oil under reduced pressure. 4-bromo-2-chloro-N-methoxy-N-methylbenzamide isolated as a light amber oil.

Workup

  1. stirringSolution stirred overnight at 23° C
  2. customReaction
  3. customthen partitioned between 2.5% NaHCO3 (250 mL) and diethyl ether (100 mL)
  4. extractionAqueous further extracted with ether (2×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated an amber oil under reduced pressure

Sources & evidence

ORD record
ord-d5ed4a33c06849c1a8e5bfa29170ba08
Source dataset
uspto-grants-2013_09
Patent number
US08524900B2

Linked notes

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