Sodium Dithionite → 5-Amino-2-morpholin-4-yl-1,3-benzoxazole

HRID 1886931Notes

Reaction equation

HRID 1886931 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][C:10]=3[N:11]=2)[CH2:3][CH2:2]1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C.O.O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[N:11]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 24489Sodium DithioniteHCID 127114612-Morpholino-5-nitrobenzo[d]oxazole

Product 1

HCID 167689435-Amino-2-morpholin-4-yl-1,3-benzoxazoleYield 30.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

A solution of 2-morpholino-5-nitrobenzo[d]oxazole (130 mg, 0.52 mmol) in ethanol/water 1:1 v/v (10 mL) was treated with sodium dithionite (182 mg, 1.04 mmol) at room temperature and then refluxed for 16 h. After cooling, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4 and evaporated to afford 35 mg (30%) of the title compound.

Workup

  1. temperaturerefluxed for 16 h
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-514e4059a9af4f5fa3b52201e8093100
Source dataset
uspto-grants-2013_08
Patent number
US08501713B2

Reaction notes

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