Benzenamine, 4-(phenylmethyl)- → N-(4-benzylphenyl)-2-fluoro-4-formylbenzamide

HRID 658979Notes

Reaction equation

HRID 658979 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:24]=[C:23]([CH:25]=[O:26])[CH:22]=[CH:21][C:17]=1[C:18](O)=[O:19].C(N(CC)C(C)C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][C:23]([CH:25]=[O:26])=[CH:24][C:16]=2[F:15])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 136914Benzenamine, 4-(phenylmethyl)-HCID 521913N,N-Diethyl-2-propanamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 184419582-Fluoro-4-formylbenzoic acid

Product 1

HCID 57625195N-(4-benzylphenyl)-2-fluoro-4-formylbenzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-benzylbenzenamine (0.100 g, 0.55 mmol), 2-fluoro-4-formylbenzoic acid (0.092 g, 0.55 mmol), N,N-diethylpropan-2-amine (0.10 ml, 0.65 mmol) in DMF (2.00ml) was added HBTU. The reaction mixture was stirred at room temperature for 1 h. The mixture was diluted with EtOAc, washed with water and dried over MgSO4. The solvent was evaporated and the residue was purified by flash chromatography in a EtOAc/Hexene system to give the title compound. MS (ESI) m/z: Calculated; 333.3: Observed; 332.1. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 10.05-10.10 (1H, m), 8.31-8.44 (2H, m), 7.80-7.85 (1H, m), 7.67-7.73 (1H, m), 7.56-7.62 (2H, m), 7.15-7.40 (6H, m), 3.99 (2H, s)

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. customThe solvent was evaporated
  4. customthe residue was purified by flash chromatography in a EtOAc/Hexene system

Sources & evidence

ORD record
ord-d15a70cd33d34da1a008da6589055c8f
Source dataset
uspto-grants-2011_12
Patent number
US08080542B2

Reaction notes

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