Methanol → 853297-25-3

HRID 576223Notes

Reaction equation

HRID 576223 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([N:8]([CH3:10])[CH3:9])=O)=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.CSC.CO>C1COCC1>[CH3:10][N:8]([CH2:6][C:5]1[CH:11]=[CH:12][C:2]([NH2:1])=[CH:3][C:4]=1[C:13]([F:14])([F:16])[F:15])[CH3:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 904155434-Amino-N,N-dimethyl-2-trifluoromethylbenzamide

Product 1

HCID 57431457853297-25-3Yield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-amino-N,N-dimethyl-2-(trifluoromethyl)benzamide (8.3 g, 23.59 mmol) in THF (100 mL) stirred under a N2 atmosphere at 20° C. was added BH3.DMS (11.20 mL, 118 mmol) dropwise. The reaction mixture was stirred at 80° C. for 2 h. To the solution was added MeOH, then concentrated in vacuo to give the crude product. The crude material was purified by silica column chromatography (DCM/MeOH=30:1). All fractions found to contain product by TLC (DCM/MeOH=10:1, Rf=0.4) were combined and concentrated to yield light yellow oil of 4-((dimethylamino)methyl)-3-(trifluoromethyl)aniline (4 g, 18.33 mmol, 78.0% yield): 1H NMR (400 MHz, CD3OD) δ 7.99 (d, J=8.0 Hz, 1H), 7.73 (s, 1H), 7.67 (d, 8.0 Hz, 1H), 4.57 (s, 2H), 2.96 (s, 6H); ES-LCMS m/z 219.2 (M+H).

Workup

  1. additionwas added BH3
  2. concentrationconcentrated in vacuo
  3. customto give the crude product
  4. customThe crude material was purified by silica column chromatography (DCM/MeOH=30:1)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8584097bc50642ef9b38d1beedd59dfa
Source dataset
uspto-grants-2015_05
Patent number
US09035063B2

Reaction notes

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