Hydrochloric Acid → HCID 135797727, compound

HRID 1350492Notes

Reaction equation

HRID 1350492 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[S:15][C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[C:12]=1[C:20]#[N:21])([O-])=O.[Sn](Cl)[Cl:23].Cl>CCO>[ClH:23].[CH:16]1[C:14]2[S:15][C:11]3[NH:10][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:1]=[C:20]([NH2:21])[C:12]=3[C:13]=2[CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 210934562-[(2-Nitrophenyl)amino]benzo[b]thiophene-3-carbonitrile

Product 1

HCID 135797727HCID 135797727, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

By using a method similar to the method of Example 532, combine 2-(2-nitro-phenylamino)-benzo[b]thiophene-3-carbonitrile (5.0 g, 17.0 mmol) and Tin(II) chloride (9.65 g, 51.0 mmol) in a mixed solvent of EtOH (50 mL) and 5.0 N HCl (50 mL), heat the suspension to reflux for 3 hours, cool to RT. The title compound 4.65 g (yield 91%) is obtained as a yellow solid by suction filtration. Mass spectrum: ACPI (m/e): 266.0 ((M+1-HCl); 1H NMR (300 MHz, DMSO-d6) ppm: 11.7 (br, 1H), 10.00 (br, 1H), 9.10 (br, 2H), 7.90–7.85 (m, 1H), 7.72–7.65 (m, 1H), 7.48–7.38 (m, 1H), 7.35–7.28 (m, 1H), 7.22–6.98 (m, 4H).

Workup

  1. temperatureheat the suspension
  2. temperatureto reflux for 3 hours

Sources & evidence

ORD record
ord-035f7c6293584f7ebb92b68f427cd007
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

Loading…