1-(Trimethylsilyl)methylamine → 4-(dibromomethyl)-3-(trifluoromethyl)-N-[(trimethylsilyl)methyl]benzamide

HRID 1692570Notes

Reaction equation

HRID 1692570 reaction equation
[Br:1][CH:2]([Br:16])[C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13].[CH3:17][Si:18]([CH3:22])([CH3:21])[CH2:19][NH2:20].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.C(OC)(C)(C)C>[Br:1][CH:2]([Br:16])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH:20][CH2:19][Si:18]([CH3:22])([CH3:21])[CH3:17])=[O:8])=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13]

Participants

6

Reactant 3

HCID 874881-(Trimethylsilyl)methylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 582709714-(Dibromomethyl)-3-(trifluoromethyl)benzoic acid

Product 1

HCID 582709764-(dibromomethyl)-3-(trifluoromethyl)-N-[(trimethylsilyl)methyl]benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4-(dibromomethyl)-3-(trifluoromethyl)benzoic acid (18.0 g, 49.7 mmol) was suspended in CH2Cl2. 1-(Trimethylsilyl)methanamine (5.1 g, 49.7 mmol) and 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (12.5 g, 54.7 mmol) were added to the solution at 0° C. The reaction mixture was stirred at room temperature over night. The reaction mixture was diluted with t-BuOMe and washed with 2M HCl, H2O, and brine. After drying over MgSO4 and evaporation, the product was found to be 22.0 g (99%).

Workup

  1. washwashed with 2M HCl, H2O, and brine
  2. dry with materialAfter drying over MgSO4 and evaporation

Sources & evidence

ORD record
ord-c6f2792f479e4b67882f4a1bbad74980
Source dataset
uspto-grants-2012_04
Patent number
US08158560B2

Reaction notes

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