Stannous Chloride → 2-Trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 1350531

반응식

HRID 1350531 반응식
[Sn](Cl)[Cl:2].[N+:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:15]=1[C:16]#[N:17])([O-])=O>Cl.C(O)C>[ClH:2].[F:23][C:22]([F:25])([F:24])[C:19]1[CH:20]=[CH:21][C:14]2[NH:13][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[N:4]=[C:16]([NH2:17])[C:15]=2[CH:18]=1

참가 물질

5

반응물 2

HCID 24479Stannous ChlorideHCID 210934552-(2-Nitro-phenylamino)-5-trifluoromethyl-benzonitrile

생성물 1

HCID 210935172-Trifluoromethyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride수율 90%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

Add a solution of tin(II) chloride (567 mg, 3 mmol) in 12 N hydrochloric acid (1.8 mL) to a solution of 2-(2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile (307 mg, 1 mmol) in ethanol (10 mL). Reflux for 24 hours, then concentrate under vacuum, add water and filter. Wash the resulting solid with water and dichloromethane then dry under vaccum to yield the titled compound as a yellow solid (282 mg, 90%): mp 334–336° C.; 1H NMR (DMSO-d6) δ 7.05–7.19 (m, 4H), 7.34 (d, 1H), 7.86 (dd, 1H), 7.87 (s, 1H), 8.79 (s, 1H), 9.26 (s, 1H), 9.75 (s, 1H), 12.40 (s, 1H). MS (ESI/neg) m/z (rel intensity) 276.1 (100).

후처리

  1. temperatureReflux for 24 hours
  2. concentrationconcentrate under vacuum
  3. additionadd water
  4. filtrationfilter
  5. washWash the resulting solid with water and dichloromethane
  6. customthen dry under vaccum

출처 및 근거

ORD 기록
ord-f29372896b9a49f4b6e4a2b1cdafa4df
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07214673B2

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