Hydroxylamine → N'-hydroxy-4-(morpholin-4-yl)-3-(trifluoromethyl)benzene-1-carboximidamide

HRID 1172955노트

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HRID 1172955 반응식
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=2[C:15]([F:18])([F:17])[F:16])[CH2:3][CH2:2]1.[NH2:19][OH:20]>C(O)C>[OH:20][N:19]=[C:11]([NH2:12])[C:10]1[CH:13]=[CH:14][C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[C:8]([C:15]([F:18])([F:17])[F:16])[CH:9]=1

참가 물질

4

반응물 2

HCID 787HydroxylamineHCID 595565444-Morpholino-3-(trifluoromethyl)benzonitrile

생성물 1

HCID 72325637N'-hydroxy-4-(morpholin-4-yl)-3-(trifluoromethyl)benzene-1-carboximidamide수율 95.5%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
65 °C

실험 절차

To a solution of 4-morpholino-3-(trifluoromethyl)benzonitrile (17.3 g, 67.3 mmol) in ethanol (400 mL) was added a 50% aqueous solution of hydroxylamine (4.9 mL, 74.1 mmol) dropwise. The mixture was heated at about 65° C. for 24 hours. The mixture was cooled to ambient temperature and the solid was removed by filtration. The fitrate was partitioned between ethyl acetate (1.8 L) and water (1.5 L). The organic layer was washed with water (1.0 L) and brine (1.0 L) and dried over anhydrous magnesium sulphate. The solvent was removed in vacuo to give N′-hydroxy-4-morpholino-3-(trifluoromethyl)benzimidamide (18.6 g, 91%) as a mixture of syn/anti isomers. LCMS (Table 1, Method b) Rt=1.85 min, m/z 290.15 (M+H)+; 1H NMR (DMSO-d6, 400 MHz) 9.75 (s, 1H), 8.09-8.16 (m, 1H), 7.89-7.96 (m, 1H), 7.52-7.58 (m, 1H), 3.66-3.72 (m, 4H), 2.83-2.93 (m, 4H).

후처리

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe solid was removed by filtration
  3. customThe fitrate was partitioned between ethyl acetate (1.8 L) and water (1.5 L)
  4. washThe organic layer was washed with water (1.0 L) and brine (1.0 L)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. customThe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-d4c73fc42cc44e96b6a50d60d0ff061f
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834039B2

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