Acetic Acid → 3-Benzylamino-4-methoxy-N-phenyl-benzamide

HRID 1859671Notes

Reaction equation

HRID 1859671 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:9][C:10]1[CH:11]=[C:12]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([NH:9][C:10]1[CH:11]=[C:12]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:13]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 84263-Amino-4-methoxybenzanilideHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 186261923-Benzylamino-4-methoxy-N-phenyl-benzamideYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzaldehyde (2.2 g, 21.0 mmol) was added to a stirred solution of 3-amino-4-methoxy-N-phenyl-benzamide (5.0 g, 21.0 mmol) in dichloromethane (250 mL) under an inert atmosphere at room temperature, followed by acetic acid (1.26 g, 21.0 mmol). After 1 hour, sodium triacetoxyborohydride (4.7 g, 21.0 mmol) was added in one portion. After 18 hours, saturated aqueous sodium bicarbonate (200 mL) was added and the mixture stirred for 2 to 3 hours. The layers were separated, the organic phase was washed with water then saturated aqueous sodium chloride, then dried over MgSO4. The solution was filtered and stripped of solvent under reduced pressure to afford the product (6.5 g); m.p. 164-165° C. after recrystallization from ethanol.

Workup

  1. waitAfter 18 hours
  2. customThe layers were separated
  3. washthe organic phase was washed with water
  4. dry with materialsaturated aqueous sodium chloride, then dried over MgSO4
  5. filtrationThe solution was filtered

Sources & evidence

ORD record
ord-3333ba2af0f34ed7a7ccdc01ee9534bf
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

Loading…