NaNCO → n-[4-(3-Amino-1,2-benzisoxazol-4-yl)phenyl]urea

HRID 560944ノート

反応式

HRID 560944 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]3[C:14]([NH2:17])=[N:15][O:16][C:12]=3[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[N-:18]=[C:19]=[O:20].[Na+]>CC(O)=O.O>[NH2:17][C:14]1[C:13]2[C:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:19]([NH2:18])=[O:20])=[CH:7][CH:6]=3)=[CH:9][CH:10]=[CH:11][C:12]=2[O:16][N:15]=1

参加物

5

反応物 2

HCID 11051568NaNCOHCID 247683944-(4-Aminophenyl)-1,2-benzoxazol-3-amine

生成物 1

HCID 11265647n-[4-(3-Amino-1,2-benzisoxazol-4-yl)phenyl]urea収率 65.2%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 962Water溶媒2 回

実験手順

A solution of Example 261A (45 mg, 0.2 mmol) and sodium isocyanate (26 mg, 0.4 mmol) in HOAc (0.5 mL) and H2O (0.5 mL) was stirred overnight at rt, then diluted with water. The precipitated solid was collected by filtration and recrystallized from THF/hexanes to give an offwhite solid (35 mg, 65%). 1H NMR (300 MHz, DMSO-D6) δ ppm 5.20 (s, 2H) 5.92 (s, 2H) 7.11 (dd, J=7.3, 0.9 Hz, 1H) 7.37 (d, J=8.5 Hz, 2H) 7.46 (dd, J=8.5, 1.0 Hz, 1H) 7.57 (d, J=8.5 Hz, 2H) 7.57 (dd, J=8.1, 7.1 Hz, 1H) 8.72 (s, 1H) MS (ESI(+)) m/e 269.0 (M+H)+.

後処理

  1. filtrationThe precipitated solid was collected by filtration
  2. customrecrystallized from THF/hexanes

出典と根拠

ORDレコード
ord-0a9e9412a79c4710841ab43033791350
出典データセット
uspto-grants-2011_11
特許番号
US08063091B2

反応ノート

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