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

HRID 518274

反応式

HRID 518274 の反応式
[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

参加物

8

反応物 5

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

生成物 1

HCID 1254086N-benzyl-5-bromo-2-methoxybenzamide収率 90.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-dd64335374804bb4a10dd1a978b38bf4
出典データセット
uspto-grants-2015_08
特許番号
US09115114B2

関連ノート

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