HCID 68629712, compound → HCID 68911546, compound

HRID 1855383Notes

Reaction equation

HRID 1855383 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:12]1[S:16][CH:15]=[N:14][CH:13]=1>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:12]1[S:16][CH:15]=[N:14][CH:13]=1

Participants

3

Reactant 1

HCID 68629712HCID 68629712, compound

Product 1

HCID 68911546HCID 68911546, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 5-(2-methoxy-4-nitro-phenyl)-thiazole (160 mg, 0.68 mmol and stannous dichloride (655 mg, 3.39 mmol) in ethanol (10 mL) was stirred at reflux temperature for 75 min. The yellow solution was evaporated under reduced pressure and the residue was dissolved in ethyl acetate. This solution is washed successively with 2N aqueous sodium hydroxide and with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residual material was triturated with dichloromethane, insoluble material was filtered off, and the filtrate was evaporated under reduced pressure to afford the title compound (128 mg, 92%) as orange oil.

Workup

  1. temperatureat reflux temperature for 75 min
  2. customThe yellow solution was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThis solution is washed successively with 2N aqueous sodium hydroxide and with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residual material was triturated with dichloromethane, insoluble material
  8. filtrationwas filtered off
  9. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-efcc0459856644c5a68af8d3ae70245c
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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