Benzhydrylamine → HCID 178434776, compound

HRID 2401389Notes

Reaction equation

HRID 2401389 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:15]([CH3:21])=[N:16][O:17][C:18]=2[CH:19]=O)=[O:7])=[CH:4][CH:3]=1.[C:24]1([CH:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[NH2:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[CH:30](/[N:31]=[CH:19]/[C:18]1[O:17][N:16]=[C:15]([CH3:21])[C:14]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]([C:5]1[CH:22]=[CH:23][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:7])([C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7036BenzhydrylamineHCID 24436Sodium SulfateHCID 86666720HCID 86666720, compound

Product 1

HCID 178434776HCID 178434776, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask was added 4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazole-5-carbaldehyde (3.86 g, 11.85 mmol), DCM (50 mL), diphenylmethanamine (2.143 mL, 12.44 mmol), and Na2SO4 (5.05 g, 35.5 mmol). The reaction was stirred at room temperature overnight before being filtered and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford the titled compound (5.61 g, 11.43 mmol) as pale yellow foam. LC/MS m/z 491 [M+H]+.

Workup

  1. filtrationbefore being filtered
  2. concentrationconcentrated
  3. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-628e2d915f264e00a6f1a40a5eabb5da
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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