Stannous Chloride → 8-Trifluoromethyl-11H-12-thia-6,11-diaza-dibenzo[a,f]azulen-5-ylamine hydrochloride

HRID 131369

반응식

HRID 131369 반응식
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[NH:14][C:15]1[S:19][C:18]2[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=2[C:16]=1[C:24]#[N:25])([O-])=O.[Sn](Cl)[Cl:27]>C(O)C.Cl>[ClH:27].[F:11][C:10]([F:13])([F:12])[C:8]1[CH:7]=[CH:6][C:5]2[NH:14][C:15]3[S:19][C:18]4[CH:20]=[CH:21][CH:22]=[CH:23][C:17]=4[C:16]=3[C:24]([NH2:25])=[N:1][C:4]=2[CH:9]=1

참가 물질

5

반응물 2

HCID 24479Stannous ChlorideHCID 586260492-(2-Nitro-4-trifluoromethyl-phenylamino)-benzo[b]thiophene-3-carbonitrile

생성물 1

HCID 1363885748-Trifluoromethyl-11H-12-thia-6,11-diaza-dibenzo[a,f]azulen-5-ylamine hydrochloride수율 97.5%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

Combine 2-(2-nitro-4-trifluoromethyl-phenylamino)-benzo[b]thiophene-3-carbonitrile (5.14 g, 14.1 mmol) and tin(II) chloride (8.05 g, 42.4 mmol) in absolute ethanol and 5N HCl (60 mL each) and reflux the suspension for 1.5 hours. Cool the reaction to ambient temperature. Collect the reaction solid by suction filtration, wash it with cold ethanol, and dry it at 40° C. under reduced pressure to give the title compound (5.083 g). Isolate a second crop of material from the initial filtrate and dry at 40° C. under reduced pressure to give the title compound (0.482 g). Total solid: 5.20 g (94.6%). Mass spectrum (APCI+, m/e): 334 (M+1-HCl); NMR (1H, 300 MHz, DMSO-d6), δ (ppm): 11.71 (s, 1H), 10.32 (s, 1H), 9.32-9.10 (m, 2H), 7.94-7.85 (m, 1H), 7.74-7.65 (m, 1H), 7.60-7.51 (m, 1H), 7.49-7.40 (m, 1H), 7.39-7.27 (m, 2H), 7.23-7.14 (m, 1H).

후처리

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. customCollect
  4. customthe reaction solid
  5. filtrationby suction filtration
  6. washwash it with cold ethanol
  7. customdry it at 40° C. under reduced pressure

출처 및 근거

ORD 기록
ord-fb758e72dd67427f88a54e2ee4668f34
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07384934B2

연결된 노트

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