Stannous chloride dihydrate → 6-Fluoro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

HRID 131381Notes

Reaction equation

HRID 131381 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-])=O)=[C:6]([NH:8][C:9]2[S:10][CH:11]=[CH:12][C:13]=2[C:14]#[N:15])[CH:7]=1.O.O.[Sn](Cl)[Cl:22]>C(O)C.Cl>[ClH:22].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:16]=[C:14]([NH2:15])[C:13]3[CH:12]=[CH:11][S:10][C:9]=3[NH:8][C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 692118502-(5-Fluoro-2-nitro-phenylamino)-thiophene-3-carbonitrile

Product 1

HCID 692151706-Fluoro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochlorideYield 83.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Suspend 2-(5-fluoro-2-nitro-phenylamino)-thiophene-3-carbonitrile (3.89 g, 14.78 mmol) in ethanol (40.0 ml). Dissolve tin(II) chloride dihydrate (10.00 g, 44.33 mmol) in 5N HCl (40.0 ml) and then add it to the suspension. Heat the reaction at reflux for 2.5 hours and then cool it to ambient temperature. Collect the resulting precipitate by vacuum filtration and then dry it under vacuum to give 3.32 g (83%) of the title compound: mass spectrum (ion spray): m/z=234.1 (M+1).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureat reflux for 2.5 hours
  4. customCollect the resulting precipitate
  5. filtrationby vacuum filtration
  6. customdry it under vacuum

Sources & evidence

ORD record
ord-eb50bd2c54b64549b7d53861da5b9f50
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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