Methanol → HCID 12790719, compound

HRID 847727Notes

Reaction equation

HRID 847727 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([OH:20])=[O:19])=[CH:14][CH:13]=2)[NH:7][C:6]1=[O:21])[CH2:2][CH2:3][CH3:4].S(Cl)(Cl)=O.[CH3:26]O>>[CH2:1]([N:5]1[C:9](=[O:10])[CH:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([O:20][CH3:26])=[O:19])=[CH:16][CH:17]=2)[NH:7][C:6]1=[O:21])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 12790725HCID 12790725, compound

Product 1

HCID 12790719HCID 12790719, compound

Procedure

3-n-Butyl-5-(4-carboxybenzyl) hydantoin (7.2 g., 0.025 mole) was added to a stirred solution of thionyl chloride (1.8 ml., 0.025 mole) in methanol (100 ml) prepared at -5° to -10° C. The mixture was allowed to come to room temperature and finally heated under reflux for 1 hour. After cooling, the clear solution was evaporated in vacuo to dryness and the resultant white crystalline solid was recrystallised from ethyl acetate to give the title compound. Yield 7.1 g (94%) m.p. 144° C.

Workup

  1. customprepared at -5° to -10° C
  2. customto come to room temperature
  3. temperaturefinally heated
  4. temperatureunder reflux for 1 hour
  5. temperatureAfter cooling
  6. customthe clear solution was evaporated in vacuo to dryness
  7. customthe resultant white crystalline solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-f5dcc54f17b44cd0839af2ac1f114022
Source dataset
uspto-grants-1981_10
Patent number
US04293563

Reaction notes

Loading…