Sodium ethoxide → 2-(3-Phthalimidopropylthio)oxazole

HRID 1834280Notes

Reaction equation

HRID 1834280 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-phthalimido-propylthio)oxazole (14 g.), m.p. 101°. Recrystallisation from ethanol give 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-562878b6b9df4d839360483c7bb92a9c
Source dataset
uspto-grants-1978_01
Patent number
US04069327

Reaction notes

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