Methanol → HCID 54337000, compound

HRID 1733306Notes

Reaction equation

HRID 1733306 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](=[CH: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])[C:8](=[CH: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 53988203HCID 53988203, compound

Product 1

HCID 54337000HCID 54337000, compound

Conditions

Temperature
40 °C

Procedure

3-n-Butyl-5-(4-carboxybenzylidene) hydantoin (5.8 g; 0.02 mole) was added gradually to a stirred mixture of thionylchloride (1.5 ml; ca 0.02 mole) in methanol (100 ml.) prepared at -10° C. The mixture was gradually warmed to 40° C. and after 1 hour was boiled under reflux for 3 hours. After cooling and storage in the refrigerator, a white solid formed and was filtered off, washed with cold methanol and dried. This solid was recrystallised from ethyl acetate to give the title compound. Yield 3.2 g; m.p. 212° C.

Workup

  1. customprepared at -10° C
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. customstorage in the refrigerator, a white solid formed
  5. filtrationwas filtered off
  6. washwashed with cold methanol
  7. customdried
  8. customThis solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-15736bca1675449d80a3440615010b56
Source dataset
uspto-grants-1980_12
Patent number
US04241073

Reaction notes

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