Benzylamine → N-benzyl-4-bromo-2-methoxybenzamide

HRID 432261Notes

Reaction equation

HRID 432261 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16](Cl)=[O:17])=[C:12]([O:19][CH3:20])[CH:11]=1.C(N(CC)CC)C>ClCCl>[CH2:1]([NH:8][C:16](=[O:17])[C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][C:12]=1[O:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 223467824-Bromo-2-methoxybenzoyl chloride

Product 1

HCID 22346886N-benzyl-4-bromo-2-methoxybenzamideYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylamine (0.69 mL, 6.31 mmol) was added slowly to a mixture of 4-Bromo-2-methoxy-1-benzenecarbonyl chloride (1.5 g, 6.01 mmol) and triethylamine (1.3 mL, 9.02 mmol) in dichloromethane (60 mL). After 3 hours, solvent was removed under reduced pressure. Ethyl acetate was added and the mixture was filtered. The filtrate was concentrated under reduced pressure and the residue was re-crystallized from ethyl acetate/heptane to give N1-benzyl-4-bromo-2-methoxybenzamide (1.654 g, 86%). 1H NMR (DMSO-d6) δ 3.92 (s, 3H), 4.67 (d, J=5.67 Hz, 32H), 7.31 (m, 7H), 8.03 (bs, 1H), 8.13 (d, J=8.41, 1H).

Workup

  1. customsolvent was removed under reduced pressure
  2. additionEthyl acetate was added
  3. filtrationthe mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was re-crystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-95e98ee7b1dc487b9121ab150653b6ad
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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