Stannous chloride dihydrate → 7-Chloro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

HRID 131379Notes

Reaction equation

HRID 131379 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][CH:11]=[CH:12][C:13]=2[C:14]#[N:15])=[C:4]([N+:16]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C.Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[S:10][CH:11]=[CH:12][C:13]=3[C:14]([NH2:15])=[N:16][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 692103022-(4-Chloro-2-nitro-phenylamino)-thiophene-3-carbonitrile

Product 1

HCID 1363885767-Chloro-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochlorideYield 142.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Suspend 2-(4-chloro-2-nitro-phenylamino)-thiophene-3-carbonitrile (4.85 g, 17.35 mmol) in ethanol (40.0 ml). Dissolve tin(II) chloride dihydrate (11.75 g, 52.06 mmol) in 5N HCl (40.0 ml) and then add it to the suspension. Heat the reaction at reflux for 48 hours. Cool the reaction to ambient temperature and then chill it in a refrigerator for 2 hours. Collect the resulting precipitate by vacuum filtration and then dry it under vacuum to give 3.53 g (71%) of the title compound: mass spectrum (ion spray): m/z=250.0 (M+1).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureat reflux for 48 hours
  4. temperatureCool
  5. customthe reaction to ambient temperature
  6. temperaturechill it in a refrigerator for 2 hours
  7. customCollect the resulting precipitate
  8. filtrationby vacuum filtration
  9. customdry it under vacuum

Sources & evidence

ORD record
ord-623c2cee87cf4f29af7e5b80f35fc012
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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