Sodium ethoxide → 2-(3-Phthalimidopropylthio)oxazole

HRID 904415Notes

Reaction equation

HRID 904415 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+].[Na].[O:21]1[CH:25]=[CH:24][N:23]=[C:22]1[SH:26]>C(O)C>[C:11]1(=[O:12])[N:10]([CH2:8][CH2:7][CH2:13][S:26][C:22]2[O:21][CH:25]=[CH:24][N:23]=2)[C:17](=[O:16])[C:18]2=[CH:2][CH:3]=[CH:4][CH:5]=[C:6]12

Participants

6

Reactant 4

HCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 21958088BromopropylphthalimideHCID 178527879HCID 178527879, compound

Product 1

HCID 129234152-(3-Phthalimidopropylthio)oxazole

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-2bc50776adaf4e3a83eaa0d4157fe448
Source dataset
uspto-grants-1980_10
Patent number
US04230865

Reaction notes

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