Stannous chloride dihydrate → HCID 11241047, compound

HRID 472153Notes

Reaction equation

HRID 472153 reaction equation
O.O.Cl[Sn]Cl.[CH3:6][C:7]1[N:8]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[C:14]([C:21]#[N:22])[CH:13]=2)[CH:9]=[CH:10][N:11]=1>Cl.[OH-].[K+]>[CH3:6][C:7]1[N:8]([C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([C:21]#[N:22])[CH:13]=2)[CH:9]=[CH:10][N:11]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 21847827HCID 21847827, compound

Product 1

HCID 11241047HCID 11241047, compoundYield 80.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
-10 °C

Procedure

SnCl2.2H2O (60.0 g; 0.26 mol) was dissolved in 37% HCl (100 mL), to this solution cooled to −10° C., 4-(2-methyl-1H-imidazol-1-yl)-2-cyano-nitrobenzene (12.0 g, 50 mmol) was added in two portions over the course of 30 min. Completed the additions the stirred reaction mixture was allowed to come to r.t., and after further 45 min. stirring, it was poured in ice/water (250 g) and 3N KOH (500 mL). The resulting suspension was filtered and the cake washed with water. The residue was suspended in 2M NH3/EtOH (250 mL), stirred for a few minutes and filtered, the filtrate was concentrated to provide the titled compound as a brown solid (8 g, 78%). C11H10N4, MW: 198.23. MS: m/z 199 (M+1). 1H-NMR (300 MHz, CDCl3) ppm: 2.21 (s, 3H), 4.70 (s, 2H), 6.79 (d, 1H), 6.97 (d, 1H), 7.22 (dd, 1H), 7.29 (d, 1H).

Workup

  1. customCompleted the additions the stirred reaction mixture
  2. customto come to r.t.
  3. filtrationThe resulting suspension was filtered
  4. washthe cake washed with water
  5. stirringstirred for a few minutes
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-08531a57b4a54b7f87a2e4f9d119ac03
Source dataset
uspto-grants-2014_01
Patent number
US08633208B2

Reaction notes

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