4-Fluorophenyl isocyanate → N-(2-methylcarbamoyl-5-tert-butylfuryl)-N'-(4-fluorophenyl)urea

HRID 1698910ノート

反応式

HRID 1698910 の反応式
[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH2:10])=[O:4].[F:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]=[C:23]=[O:24])=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[O:6][C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:8][C:9]=1[NH:10][C:23]([NH:22][C:19]1[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=1)=[O:24])=[O:4]

参加物

4

反応物 2

HCID 709554-Fluorophenyl isocyanateHCID 18322380N-methyl-3-amino-5-tert-butyl-2-furancarboxamide

生成物 1

HCID 9923703N-(2-methylcarbamoyl-5-tert-butylfuryl)-N'-(4-fluorophenyl)urea収率 63.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of N-methyl-3-amino-5-tert-butylfuran-2-carboxamide (0.15 g, 0.76 mmol) in anh. toluene (2 mL) at the reflux temp. was slowly added 4-fluorophenyl isocyanate (0.10 g, 0.76 mmol, 1.0 equiv). The resulting solution was allowed to stir at the reflux temp. for 14 h, cooled to room temp., and concentrated under reduced pressure. The residue was purified by flash chromatography (15 g SiO2, gradient from 50% CH2Cl2/hexane to 100% CH2Cl2, then to 20% EtOAc/CH2Cl2) to afford N-(2-methylcarbamoyl-5-tert-butylfuryl)-N′-(4-fluorophenyl)urea (0.16 g, 61%): mp 109-11° C., TLC (30% EtOAc/CH2Cl2) Rf0.21; 1H NMR (CDCl3) δ1.29 (s, 9H), 2.89 (d, J=4.8 Hz, 3H), 6.02 (br q, J=4.8 Hz, 1H), 6.98 (app td, J=16.6, 4.1 Hz, 2H), 7.01 (s, 1H), 7.34-7.39 (m, 2H), 8.05 (br s, 1H), 9.14 (s, 1H); 13C NMR (CDCl3) δ25.5, 28.7 (3C), 33.1, 100.7, 115.6 (d, JC-F=23.2 Hz, 2C), 121.5 (d, JC-F=7.3 Hz, 2C), 128.3, 134.5 (br s), 152.4, 158.9 (d, JC-F=242.9 Hz, 1C), 161.6, 165.8; FAB-LRMS m/z (rel abundance) 334 (M+H, 100%).

後処理

  1. temperaturecooled to room temp.
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (15 g SiO2, gradient from 50% CH2Cl2/hexane to 100% CH2Cl2

出典と根拠

ORDレコード
ord-ce74755e9c98424e814374a84940b3fe
出典データセット
uspto-grants-2002_02
特許番号
US06344476B1

反応ノート

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