p-Toluenesulfonic acid → HCID 12803432, compound

HRID 371772Notes

Reaction equation

HRID 371772 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[NH:6][C:5]1=[O:15].[C:16](OC(=O)C)(=[O:18])[CH3:17].C1(C)C=CC(S(O)(=O)=O)=CC=1.N1CCNC1=O>>[C:16]([O:1][CH2:2][CH2:3][N:4]1[CH2:8][CH:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:6][C:5]1=[O:15])(=[O:18])[CH3:17]

Participants

5

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 7918Acetic AnhydrideHCID 84532-ImidazolidinoneHCID 12534479HCID 12534479, compound

Product 1

HCID 12803432HCID 12803432, compound

Procedure

Approximately 9.2 g of 1-(2-hydroxyethyl-4-phenyl-2-imidazolidone is stirred with acetic anhydride (25 ml.) and p-toluenesulfonic acid (200 mg.) for 4 hours, during which time the imidazolidone completely dissolves. The solution (100 ml.) from which a white solid precipitates. The solid is extracted with methylene chloride (3×100 ml.). The organic layer is separated, dried and the solvent removed to give a pale yellow solid. Recrystallization from ether gives the title compound as a white crystalline solid; m.p. 88°-90° C.

Workup

  1. dissolutioncompletely dissolves
  2. customThe solution (100 ml.) from which a white solid precipitates
  3. extractionThe solid is extracted with methylene chloride (3×100 ml.)
  4. customThe organic layer is separated
  5. customdried
  6. customthe solvent removed
  7. customto give a pale yellow solid
  8. customRecrystallization from ether

Sources & evidence

ORD record
ord-510079da7f8a41c6b9cbf79e847eedb8
Source dataset
uspto-grants-1978_05
Patent number
US04087611

Reaction notes

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