Benzylamine → N-benzyl-5-bromo-2-methoxybenzamide

HRID 575544Notes

Reaction equation

HRID 575544 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH2:13]([NH2:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.N(C(C)C)(C(C)C)CC>CN(C=O)C.C(Cl)Cl>[CH2:13]([NH:20][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[O:11][CH3:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

8

Reactant 5

HCID 7504BenzylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 8817395-Bromo-2-methoxybenzoic acid

Product 1

HCID 1254086N-benzyl-5-bromo-2-methoxybenzamideYield 90.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To an ice bath cooled mixture of 5-bromo-2-methoxybenzoic acid (439 mg, 1.9 mmol) in 1:1 CH2Cl2:DMF (4 mL) was added benzylamine (0.228 mL, 2.1 mmol), EDCI (438 mg, 2.3 mmol), HOBt (311 mg, 2.3 mmol) and NEtiPr2 (0.496 mL, 2.85 mmol). The mixture was then stirred at room temperature until the reaction was complete. Extractive work up with ethyl acetate, washing with saturated aqueous NaHCO3, H2O, saturated aqueous KHSO4 and brine, gave the title compound (550 mg) after isolation which was carried forward without purification. LCMS (M+H)+ 320, 322.

Workup

  1. temperatureTo an ice bath cooled
  2. washExtractive work up with ethyl acetate, washing with saturated aqueous NaHCO3, H2O, saturated aqueous KHSO4 and brine

Sources & evidence

ORD record
ord-9968fe7574054c03bcfd412b85384925
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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