Thionyl Chloride → HCID 178449295, compound

HRID 744709Notes

Reaction equation

HRID 744709 reaction equation
[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14](O)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:15][CH2:16][C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O>C(Cl)Cl>[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:15][CH2:16][C:17]2[N:18]=[CH:19][NH:20][CH:21]=2)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178449308HCID 178449308, compound

Product 1

HCID 178449295HCID 178449295, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[3-(4-tert-butylaminocarbonylphenyl)-3-hydroxy-3-phenylpropyl]-1H-imidazole (2,5 g, 6,6 mmol) is dissolved in methylene chloride (50 ml) and thionyl chloride (3,2 g, 26,9 mmol) is added to the solution. The mixture is refluxed for two hours. The solvents are evaporated. 2M sodium hydroxide is added to the residue and the product is extracted into ethyl acetate and dried. The product is convened to its HCl salt with dry hydrogen chloride gas and the solvent is evaporated. Yield 2,14 g, 91%.

Workup

  1. temperatureThe mixture is refluxed for two hours
  2. customThe solvents are evaporated
  3. addition2M sodium hydroxide is added to the residue
  4. extractionthe product is extracted into ethyl acetate
  5. customdried
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-c7adb761d96c4ff5a0e7061425a57224
Source dataset
uspto-grants-1996_09
Patent number
US05559141

Reaction notes

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