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

HRID 7718

반응식

HRID 7718 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 57417360Sodium chloride; water용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-6548a23538894aa79436e59d15d367bc
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087601B2

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