1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2-Amino-4-fluorobenzamide

HRID 625785

反応式

HRID 625785 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C1C=CC2N(O)N=[N:18]C=2C=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C.N.CO>CN(C=O)C>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:18])=[O:5]

参加物

7

反応物 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27249674-Fluoroanthranilic acidHCID 21705897Ammonia methanol

生成物 1

HCID 102410042-Amino-4-fluorobenzamide収率 72.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To solution of 2-amino-4-fluorobenzoic acid (4.0 g, 25.8 mmol) in degassed DMF (50 mL) were added HOBt (4.19 g, 31 mmol), DIEA (5.4 mL, 31 mmol), EDCI (5.94 g, 31 mmol) and 2N NH3/MeOH (18 mL, 36.1 mmol). The solution was stirred at rt for 48 h, and then concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford 2-amino-4-fluorobenzamide as a solid (2.89 g, 66%). 1H NMR (300 MHz, DMSO-d6) δ 6.28 (m, 1H), 6.44 (m, 1H), 6.90 (br s, 2H), 7.08 (m, 1H), 7.58 (m, 1H), 7.71 (br d, 1H).

後処理

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-1a734152fcc34c9aafc56644849d0576
出典データセット
uspto-grants-2016_04
特許番号
US09308207B2

関連ノート

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