Stannous Chloride → 7-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

HRID 131309Notes

Reaction equation

HRID 131309 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[S:10][C:11]([CH3:16])=[CH:12][C:13]=2[C:14]#[N:15])=[C:4]([N+:17]([O-])=O)[CH:3]=1.[Sn](Cl)Cl.Cl.O>C(O)C.O>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[S:10][C:11]([CH3:16])=[CH:12][C:13]=3[C:14]([NH2:15])=[N:17][C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 21885828Hydrate;hydrochlorideHCID 586259752-(4-Chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile

Product 1

HCID 1363885727-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochlorideYield 221.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Suspend 2-(4-chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile (2.92 g) in ethanol (40 ml), add anhydrous tin(II)chloride(5 g,) in 1:1 concentrated hydrochloric acid/water (32 ml) and heat the mixture under reflux for 2 hours. Dilute the mixture with water and allow to cool. Collect the precipitate formed by filtration and dry under high vacuum to give 7-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride as a yellow solid (3.3 g, 90%): mass Spectrum (FIA) 264/266 (M+1).

Workup

  1. temperatureheat the mixture
  2. temperatureunder reflux for 2 hours
  3. temperatureto cool
  4. customCollect the precipitate
  5. customformed by filtration
  6. customdry under high vacuum

Sources & evidence

ORD record
ord-c65fa74572a64b97b354ded09e29b853
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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