Water → HCID 19900723, compound

HRID 1029514Notes

Reaction equation

HRID 1029514 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]=[C:9]1[CH:25]=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:27](O)[CH2:28][CH2:29][OH:30].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>C1(C)C=CC=CC=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:10]=[C:9]1[CH:25]1[O:30][CH2:29][CH2:28][CH2:27][O:26]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 962WaterHCID 104421,3-Propanediol2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19900725HCID 19900725, compound

Product 1

HCID 19900723HCID 19900723, compoundYield 90.4%

Reagents, catalysts & solvents 4

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-benzyl-2-formyl-4,5-diphenyl-imidazole (6.8 g), propane-1,3-diol (7.6 g) and polymer-bound pyridinium 4-toluenesulphonate (1.0 g) in toluene (250 ml) was stirred at reflux under a Dean & Stark water trap for 8 hours. TLC analysis (using a 1:1 v/v mixture of ethyl acetate and hexane) showed about 20% unreacted aldehyde. A further quantity of polymer-bound pyridinium 4-toluenesulphonate (250 mg) and propane-1,3-diol (3.5 g) were added, and the mixture was heated at reflux for a further period of 6 hours. After cooling to room temperature the mixture was decanted from the catalyst and washed with water (3×100 ml). The organic solution was dried over magnesium sulphate and evaporated, to give 1-benzyl-2-(1,3-dioxan-2-yl)-4,5-diphenylimidazole (7.2 g), in the form of a pale pink solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for a further period of 6 hours
  3. customwas decanted from the catalyst
  4. washwashed with water (3×100 ml)
  5. dry with materialThe organic solution was dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-17dadac4d39b4cf1adaf84b28d7366c3
Source dataset
uspto-grants-1992_04
Patent number
US05102900

Reaction notes

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