Tin tetrachloride → HCID 20785103, compound

HRID 2182434Notes

Reaction equation

HRID 2182434 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)(Cl)(Cl)Cl.C(=O)([O-])O.[Na+]>C(O)C>[CH2:1]([NH:8][C:9]1[C:10]([NH2:19])=[CH:11][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 7923012HCID 7923012, compound

Product 1

HCID 20785103HCID 20785103, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of benzyl-(4-methanesulfonyl-2-nitro-phenyl)-amine (0.300 g, Reference Example 66) and tin chloride (1.86 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 N*1*-benzyl-4-methanesulfonyl-benzene-1,2-diamine (0.255 g) as a pale brown solid. LC-MS (METHOD B): RT=2.74 minutes, 275.20 (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-7daee55d23d34d5aad7b97ee59dd5d78
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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