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

HRID 131369

反応式

HRID 131369 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fb758e72dd67427f88a54e2ee4668f34
出典データセット
uspto-grants-2008_06
特許番号
US07384934B2

関連ノート

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