Stannous Chloride → 6-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

HRID 131307Notes

Reaction equation

HRID 131307 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:17]([O-])=O)=[C:6]([NH:8][C:9]2[S:10][C:11]([CH3:16])=[CH:12][C:13]=2[C:14]#[N:15])[CH:7]=1.[Sn](Cl)Cl>C(O)C.Cl.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:17]=[C:14]([NH2:15])[C:13]3[CH:12]=[C:11]([CH3:16])[S:10][C:9]=3[NH:8][C:6]=2[CH:7]=1

Participants

6

Reactant 2

HCID 24479Stannous ChlorideHCID 586260242-(5-Chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile

Product 1

HCID 692144886-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochlorideYield 180.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Suspend 2-(5-chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile (0.58 g, 1.98 mmol) in ethanol (20 ml), add anhydrous tin(II)chloride(1.5 g, 6.66 mmol) in concentrated hydrochloric acid (6 ml) and heat the mixture under reflux for 75 minutes. Dilute the mixture with water and allow to cool. Collect the precipitate by filtration and dry under high vacuum to give 6-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride as a yellow solid (0.537 g, 90%): Mass Spectrum (FIA) 300/302 (M+1).

Workup

  1. temperatureheat the mixture
  2. temperatureunder reflux for 75 minutes
  3. temperatureto cool
  4. customCollect the precipitate
  5. filtrationby filtration
  6. customdry under high vacuum

Sources & evidence

ORD record
ord-4dae3d9cbde84c11a3e4208cc091ae2d
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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