Reaction equation
[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]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- temperatureCool
- customthe reaction to ambient temperature
- customCollect
- customthe reaction solid
- filtrationby suction filtration
- washwash it with cold ethanol
- customdry it at 40° C. under reduced pressure
Sources & evidence
- ORD record
- ord-fb758e72dd67427f88a54e2ee4668f34
- Source dataset
- uspto-grants-2008_06
- Patent number
- US07384934B2
Linked notes
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