Stannous chloride dihydrate → HCID 9968420, compound

HRID 1369634Notes

Reaction equation

HRID 1369634 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=4)=[CH:15][C:8]=23)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl>CCO.Cl>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=4)=[CH:15][C:8]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 18516291HCID 18516291, compound

Product 1

HCID 9968420HCID 9968420, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

To a suspension of Example 272A (0.13 g, 0.34 mmnol) in EtOH (3.5 mL), a solution of tin(II) chloride dihydrate (0.31 g, 1.36 mmol) in conc. HCl (0.68 mL) was slowly added. The reaction was stirred for 22 hours and partitioned between dichloromethane (75 mL) and 1 N NaOH (75 mL). The organic layer was washed with 1 N NaOH (1×50 mL), brine (1×50 mL), partially dried (Na2SO4), and concentrated to a colored solid (0.13 g). The desired product was crystallized from acetonitrile to yield colored crystals (0.08 g, 68%).

Workup

  1. custompartitioned between dichloromethane (75 mL) and 1 N NaOH (75 mL)
  2. washThe organic layer was washed with 1 N NaOH (1×50 mL), brine (1×50 mL)
  3. dry with materialpartially dried (Na2SO4)
  4. concentrationconcentrated to a colored solid (0.13 g)
  5. customThe desired product was crystallized from acetonitrile

Sources & evidence

ORD record
ord-fd0de889968c403d8dfff42c31ff9d9f
Source dataset
uspto-grants-2003_06
Patent number
US06579882B2

Reaction notes

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