Stannous chloride dihydrate → 4-[2-(5-Amino-2-methyl-phenylamino)-oxazol-5-yl]-benzonitrile

HRID 244588Notes

Reaction equation

HRID 244588 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12]1[O:13][C:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=2)=[CH:15][N:16]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:11][C:12]2[O:13][C:14]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)=[CH:15][N:16]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 248719944-[2-(2-Methyl-5-nitro-phenylamino)-oxazol-5-yl]-benzonitrile

Product 1

HCID 177573464-[2-(5-Amino-2-methyl-phenylamino)-oxazol-5-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[2-(2-Methyl-5-nitro-phenylamino)-oxazol-5-yl]-benzonitrile (500 mg, 1.56 mmol) in ethanol (15 mL) was added tin(II) chloride dihydrate (677 mg, 3 mmol). The reaction mixture was heated under reflux for 4 h. The mixture was then concentrated, saturated aqueous NaHCO3 was added and the resultant suspension was extracted with ethyl acetate (3×15 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous MgSO4 and concentrated. The residue was alumina column chromatographed (dichloromethane/ethanol: 99/1). 4-[2-(5-Amino-2-methyl-phenylamino)-oxazol-5-yl]-benzonitrile was obtained as pale yellow powder (172 mg, 38%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationThe mixture was then concentrated
  4. additionsaturated aqueous NaHCO3 was added
  5. extractionthe resultant suspension was extracted with ethyl acetate (3×15 mL)
  6. washThe combined organic layers were washed with brine (30 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customchromatographed (dichloromethane/ethanol: 99/1)

Sources & evidence

ORD record
ord-0a083d89110e4385829ac84497302976
Source dataset
uspto-grants-2014_02
Patent number
US08658659B2

Reaction notes

Loading…