Hydrochloric Acid → 8,9-Di-fluoro-11H-12-thia-6,11-diaza-dibenzo[a,f]azulen-5-ylamine hydrogenchloride

HRID 131377Notes

Reaction equation

HRID 131377 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH:9][C:10]2[S:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[C:11]=2[C:19]#[N:20])=[C:4]([N+:21]([O-])=O)[CH:3]=1.[Sn](Cl)[Cl:25].Cl>CCO>[ClH:25].[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]2[NH:9][C:10]3[S:14][C:13]4[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=4[C:11]=3[C:19]([NH2:20])=[N:21][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 184222662-(4,5-Difluoro-2-nitro-phenylamino)-benzo[b]thiophene-3-carbonitrile

Product 1

HCID 1363885758,9-Di-fluoro-11H-12-thia-6,11-diaza-dibenzo[a,f]azulen-5-ylamine hydrogenchloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 2-(4,5-difluoro-2-nitro-phenylamino)-benzo[b]thiophene-3-carbonitrile (2.03 g, 6.13 mmol) and Tin(II) chloride (3.49 g, 18.4 mmol) in a mixed solvent of EtOH (20 mL) and 5.0 N HCl (20 mL), heat the suspension to reflux for overnight, cool to RT. The title compound 2.05 g btaine as a yellow solid by suction filtration. 1H NMR (300 MHz, DMSO-d6): δ 11.56 (br, 1H), 10.06 (br, 1H), 9.14 (br, 2H), 7.96-7.85 (m, 1H), 7.71-7.64 (m, 1H), 7.49-7.42 (m, 1H), 7.34-7.29 (m, 1H), 7.22-7.16 (m, 1H), 7.11-7.04 (m, 2H).

Workup

  1. temperatureto reflux for overnight
  2. filtrationThe title compound 2.05 g btaine as a yellow solid by suction filtration

Sources & evidence

ORD record
ord-9cec262123a84526bc07de8fd3fd55a6
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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