Sodium ethoxide → 2-(3-Phthalimidopropylthio)oxazole

HRID 2397749Notes

Reaction equation

HRID 2397749 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°-3°.

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-aabff3cf2db04a53b023d5f1abb1b8c8
Source dataset
uspto-grants-1977_05
Patent number
US04022797

Reaction notes

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