Water → 4-bromo-3-methyl-N-(trimethylsilylmethyl)benzamide

HRID 241524

Reaction equation

HRID 241524 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][C:3]=1[CH3:11].CN(C)CCCN=C=NCC.[NH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26].O>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:7])=[CH:4][C:3]=1[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 821314-Bromo-3-methylbenzoic acidHCID 874881-(Trimethylsilyl)methylamine

Product 1

HCID 668364694-bromo-3-methyl-N-(trimethylsilylmethyl)benzamideYield 94%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 4-bromo-3-methylbenzoic acid (25 g) and 4-(dimethylamino)pyridine (“DMAP”, 2.1 g) in CH2Cl2 (320 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (“EDC”, 22.4 g) portionwise. Then, (aminomethyl)trimethylsilane (8.6 mL) was added, while cooling to keep the internal temperature below 20° C. The reaction was stirred at room temperature overnight. Water was added under vigorous stirring, and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phase dried (Na2SO4), and filtered over silica gel using CH2Cl2 and methyl tert-butyl ether (MTBE) to afford the title compound (32.8 g, 94%).

Workup

  1. temperaturewhile cooling
  2. customthe internal temperature below 20° C
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted twice with CH2Cl2
  5. dry with materialthe combined organic phase dried (Na2SO4)
  6. filtrationfiltered over silica gel

Sources & evidence

ORD record
ord-84bff735b8e84773b38a246cec69f299
Source dataset
uspto-grants-2014_02
Patent number
US08653000B2

Linked notes

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