Sodium ethoxide → 2-(3-Phthalimidopropylthio)oxazole

HRID 847888Notes

Reaction equation

HRID 847888 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]1C=C[CH:13]=[C:7]2[C:8]([NH:10][C:11](=[O:12])[C:6]=12)=O.[O-:16][CH2:17][CH3:18].[Na+].[O:20]1[CH:24]=[CH:23][N:22]=[C:21]1[SH:25]>C(O)C>[C:11]1(=[O:12])[N:10]([CH2:8][CH2:7][CH2:13][S:25][C:21]2[O:20][CH:24]=[CH:23][N:22]=2)[C:17](=[O:16])[C:18]2=[CH:2][CH:3]=[CH:4][CH:5]=[C:6]12

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 21958088BromopropylphthalimideHCID 178527879HCID 178527879, compound

Product 1

HCID 129234152-(3-Phthalimidopropylthio)oxazoleYield 287.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Bromopropylphthalimide (13.4 g.) was added to a stirred solution of sodium ethoxide (from 1.15 g. sodium) and oxazole-2-thiol (5.1 g.) in ethanol (100 ml.). The resultant solution was heated under reflux for 2.5 hours and concentrated under reduced pressure. The residue was triturated with water (100 ml.) to afford 2-(3-phthalimidopropylthio)oxazole (14 g.), m.p. 101°. Recrystallisation from ethanol gave the pure oxazole, m.p. 102°-103°.

Workup

  1. temperatureunder reflux for 2.5 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with water (100 ml.)

Sources & evidence

ORD record
ord-4618564391eb4eb4b9e0f494912fc339
Source dataset
uspto-grants-1981_10
Patent number
US04293697

Reaction notes

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