Water → 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

HRID 1844639

Reaction equation

HRID 1844639 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[Cl:11].Cl.CN(C)CCCN=C=NCC.[CH3:24][Si:25]([CH2:28][NH2:29])([CH3:27])[CH3:26].O>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:29][CH2:28][Si:25]([CH3:27])([CH3:26])[CH3:24])=[O:7])=[CH:4][C:3]=1[Cl:11]

Participants

6

Reactant 4

HCID 962WaterHCID 874881-(Trimethylsilyl)methylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 125943024-Bromo-3-chlorobenzoic acid

Product 1

HCID 668366994-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-bromo-3-chloro-benzoic acid (commercially available) (5.0 g) in dichloromethane (30 ml) was added N-(−3-dimethylaminopropyl)-N′-ethylcarbodiimid hydrochloride (5.29 g), N,N-dimethylaminopyridine (1.19 g) and trimethylsilylmethylamine (2.85 ml). The reaction mixture was stirred at ambient temperature for 5 hours. Water and dichloromethane was added to the reaction mixture. The phases were separated and the organic phase was washed with brine, dried over sodium sulfate and filtered through silica gel. The reaction mixture was concentrated to give 4-bromo-3-chloro-N-trimethylsilanylmethyl-benzamide (4.87 g). 1H-NMR (400 MHz, CDCl3): 7.68 (d, 1H), 7.55 (s, 1H), 7.33 (d, 1H), 5.85 (s, 1H), 2.84 (d, 2H), 0.00 (s, 9H) ppm.

Workup

  1. customThe phases were separated
  2. washthe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered through silica gel
  5. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a3c1a6b6daf04fb9b085f17a021f3c52
Source dataset
uspto-grants-2015_02
Patent number
US08946447B2

Linked notes

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