Sodium ethoxide → 2-(3-Phthalimidopropylthio)oxazole

HRID 972612Notes

Reaction equation

HRID 972612 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-b24337b210b74768b370fa733b6f47ad
Source dataset
uspto-grants-1977_10
Patent number
US04053473

Reaction notes

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