Reaction #218491

ord-c65fa74572a64b97b354ded09e29b853

Reaction equation

Cc1cc(C#N)c(Nc2ccc(Cl)cc2[N+](=O)[O-])s1
2-(4-chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile
[Cl][Sn][Cl]
tin(II)chloride
Cl.O
hydrochloric acid water
→
Cc1cc2c(s1)Nc1ccc(Cl)cc1N=C2N.Cl
7-chloro-2-methyl-4H-3-thia-4,9-diaza-benzo[f]azulen-10-ylamine hydrochloride

Reactants

Cc1cc(C#N)c(Nc2ccc(Cl)cc2[N+](=O)[O-])s1
2-(4-chloro-2-nitro-phenylamino)-5-methyl-thiophene-3-carbonitrile
[Cl][Sn][Cl]
tin(II)chloride
Cl.O
hydrochloric acid water

Reagents

None

Solvents

CCO
ethanol
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperatureheat the mixture
  2. 2
    Temperatureunder reflux for 2 hours
  3. 3
    Temperatureto cool
  4. 4
    OtherCollect the precipitate
  5. 5
    Otherformed by filtration
  6. 6
    Otherdry under high vacuum

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07384934B2uspto-grants-2008_06