Water → HCID 12767212, compound

HRID 904140Notes

Reaction equation

HRID 904140 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[CH:8]([CH:11](O)[CH3:12])[NH:7][C:6]1=[O:14])[CH2:2][CH2:3][CH3:4].CS(O)(=O)=O.O>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[C:9](=[O:10])/[C:8](=[CH:11]/[CH3:12])/[NH:7][C:6]1=[O:14])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 6395Methanesulfonic AcidHCID 12942450HCID 12942450, compound

Product 1

HCID 12767212HCID 12767212, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (1' RS, 5 SR)-3-n-butyl-5-(1-hydroxyethyl)hydantoin (7.7 g 0.039 mole) in toluene (150 ml) containing methane sulphonic acid (2.5 mole 0.039 mole) was heated under a Dean and Stark apparatus for 48 hours during which time 0.65 ml of water collected (94% of theory). The mixture was cooled to room-temperature and washed with dilute sodium bicarbonate and dried (MgSO4). Removal of the solvent gave a solid which was crystallised from cyclohexane to give the title compound as prisms m.p. 127° C. Yield=3.3 g=46.5%. The following Examples 14-20 illustrate pharmaceutical formulations containing the compound 3-n-butyl-5-methylenehydantoin.

Workup

  1. customcollected (94% of theory)
  2. temperatureThe mixture was cooled to room-temperature
  3. washwashed with dilute sodium bicarbonate
  4. dry with materialdried (MgSO4)
  5. customRemoval of the solvent
  6. customgave a solid which
  7. customwas crystallised from cyclohexane

Sources & evidence

ORD record
ord-a634587b3ce3489698a0bcd78f763ce6
Source dataset
uspto-grants-1980_10
Patent number
US04230709

Reaction notes

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