Water → [4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile

HRID 7718

反応式

HRID 7718 の反応式
[C-]#N.[Na+].Br[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)=[CH:8][C:7]=1[Cl:21].[CH3:22][N:23](C=O)C.O>[Cl-].[Na+].O>[O:13]1[C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=[C:12]1[C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:22]#[N:23])=[C:7]([Cl:21])[CH:8]=1

参加物

6

反応物 4

HCID 962WaterHCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 219909852-[4-(Bromomethyl)-3-chlorophenyl]-1,3-benzoxazole

生成物 1

HCID 10286072[4-(1,3-Benzoxazol-2-yl)-2-chlorophenyl]acetonitrile

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

実験手順

A slurry of NaCN (435 mg, 8.9 mmol), 2-[4-(bromomethyl)-3-chlorophenyl]-1,3-benzoxazole (940 mg, 2.9 mmol), DMF (30 mL) and H2O (30 mL) was stirred at rt for 12 h. The reaction mixture was poured into brine (250 mL) and filtered. The resultant colorless solid was purified by flash chromatography on silica gel (EtOAc:hexanes 1:9) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-chlorophenyl]acetonitrile as a colorless solid: 1H NMR (CDCl3, 300 MHz) δ 8.32 (s, 1H), 8.19 (dd, 1H), 7.77–7.80 (m, 1H), 7.70 (d, 1H), 7.59–7.61 (m, 1H), 7.38–7.41 (m, 2H), 3.92 (s, 2H). MS (ESI) 269 (M+H)+.

後処理

  1. filtrationfiltered
  2. customwas purified by flash chromatography on silica gel (EtOAc:hexanes 1:9)

出典と根拠

ORDレコード
ord-6548a23538894aa79436e59d15d367bc
出典データセット
uspto-grants-2006_08
特許番号
US07087601B2

関連ノート

読み込み中…