Stannous Chloride → HCID 22558446, compound

HRID 984437Notes

Reaction equation

HRID 984437 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:32])[C:16]([NH:18][C:19]([CH3:31])([CH3:30])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=2)=[O:17])[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][CH:12]=[N:11][CH:10]=1.[Sn](Cl)Cl.O1CCOCC1>C(O)C.C(OCC)(=O)C>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][C:19]([NH:18][C:16](=[O:17])[C:15]([NH:14][C:5]2[CH:6]=[CH:7][C:8]([C:9]3[O:13][CH:12]=[N:11][CH:10]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:32])([CH3:30])[CH3:31])=[CH:22][CH:23]=1

Participants

6

Reactant 3

HCID 24479Stannous ChlorideHCID 312751,4-DioxaneHCID 9803166HCID 9803166, compound

Product 1

HCID 22558446HCID 22558446, compoundYield 75.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 44 mg (0.1 mmol) of N-[3-methoxy-4-(5-oxazolyl)phenyl]-N′-[1,1-dimethyl-2-(4-nitrophenyl)ethyl]oxalamide and 90 mg (0.5 mmol) of tin(II) chloride were stirred and heated at 85° C. in 2 ml of ethanol and 1 ml of 1,4-dioxane for 5 hours. The resulting solution was cooled, diluted with ethyl acetate and washed with 2M sodium hydroxide. The organic phase was dried over magnesium sulphate, evaporated to dryness and the residue chromatographed on silica gel using ethyl acetate/petrol (2:1) for the elution. After trituration with petrol there was obtained 31 mg of N-[2-(4-aminophenyl)-1,1-dimethylethyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide as a white solid. MS: m/e 409 M+H]+.

Workup

  1. temperatureThe resulting solution was cooled
  2. washwashed with 2M sodium hydroxide
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. customevaporated to dryness
  5. customthe residue chromatographed on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-af9f12b28cf94cd993fcb6ee81950467
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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