Hydrochloric Acid → 12-Amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine hydrochloride

HRID 131373Notes

Reaction equation

HRID 131373 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-])=O)=[C:6]([NH:8][C:9]2[S:13][C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[C:10]=2[C:18]#[N:19])[CH:7]=1.O.O.[Sn](Cl)[Cl:26].Cl>CCO>[ClH:26].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:20]=[C:18]([NH2:19])[C:10]3[C:11]4[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=4[S:13][C:9]=3[NH:8][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 184222432-(5-Fluoro-2-nitroanilino)benzo[b]thiophene-3-carbonitrile

Product 1

HCID 1842238412-Amino-8-fluoro-6H-[1]benzothieno[2,3-b][1,5]benzodiazepine hydrochlorideYield 78.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Combine 2-(5-fluoro-2-nitro-phenylamino)-benzo[b]thiophene-3-carbonitrile (2.15 g, 6.87 mmol) and Tin(II) chloride, dihydrate (4.65 g, 20.6 mmol) in a mixed solvent of EtOH (25 mL) and 5.0 N HCl (25 mL), heat the suspension to reflux for 3 hours, cool to RT. Suction filtration obtains the title compound 1.73 g (yield 78%) as a yellow solid by. Mass spectrum: ACPI (m/e): 284((M+1-HCl); 1H NMR (300 MHz, DMSO-d6) δ 11.46 (br, 1H), 10.02 (br, 1H), 9.02 (br, 2H), 7.90-7.87 (m, 1H), 7.71-7.68 (m, 1H), 7.46-7.40 (m, 1H), 7.33-7.28 (m, 1H), 7.12-6.94 (m, 2H), 6.85-6.81(m, 1H).

Workup

  1. temperatureto reflux for 3 hours
  2. filtrationSuction filtration

Sources & evidence

ORD record
ord-2edbba338bce44df924d566160fa8464
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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