Tin tetrachloride → HCID 178422351, compound

HRID 2182376Notes

Reaction equation

HRID 2182376 reaction equation
[Cl:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]2[NH:6][C:7]([C:9]3[C:13]([N+:14]([O-])=O)=[CH:12][NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1.[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(O)C>[Cl:1][C:2]1[C:18]([CH3:19])=[CH:17][C:5]2[NH:6][C:7]([C:9]3[C:13]([NH2:14])=[CH:12][NH:11][N:10]=3)=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 178422352HCID 178422352, compound

Product 1

HCID 178422351HCID 178422351, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 5-chloro-6-methyl-2-(4-nitro-1H-pyrazol-3-yl)-1H-benzoimidazole [0.320 g, Example 249(g)] and tin chloride (1.10 g) in ethanol (5 ml) was heated in a Smith Creator microwave at 140° C. for 10 minutes. The reaction mixture was basified using saturated sodium hydrogen carbonate solution to pH 8 and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated to give 3-(5-chloro-6-methyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-ylamine as a pale brown solid. LC-MS (METHOD B): RT=2.28 minutes, 248.13 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-178c1d25ffb7475e97c36f2ad4522ea3
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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