Morpholine → 2-{5-[(Morpholin-4-yl)methyl]thiophen-2-yl}-5-nitro-1,3-benzoxazole

HRID 918069Notes

Reaction equation

HRID 918069 reaction equation
Br[CH2:2][C:3]1[S:7][C:6]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=3[N:12]=2)=[CH:5][CH:4]=1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>C1C=CC=CC=1>[N:20]1([CH2:2][C:3]2[S:7][C:6]([C:8]3[O:9][C:10]4[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:11]=4[N:12]=3)=[CH:5][CH:4]=2)[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 12781927HCID 12781927, compound

Product 1

HCID 127819302-{5-[(Morpholin-4-yl)methyl]thiophen-2-yl}-5-nitro-1,3-benzoxazoleYield 91.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2-(5-Bromomethyl-2-thienyl)-5-nitrobenzoxazole (2.0 g, 0.006 mole) and morpholine (2.6 g, 0.03 mole) are dissolved in 100 ml of benzene and heated at reflux for 36 hours. The precipitated morpholine hydrobromide is removed by filtration and the benzene is evaporated yielding an oil. Crystallization from ethanol yields 1.9 g of product, melting point 149°-151°C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 36 hours
  3. customThe precipitated morpholine hydrobromide is removed by filtration
  4. customthe benzene is evaporated
  5. customyielding an oil
  6. customCrystallization from ethanol

Sources & evidence

ORD record
ord-f1b38445cf5f441487c3dd4c2a470278
Source dataset
uspto-grants-1976_07
Patent number
US03969351

Reaction notes

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