1-(p-N-tert-butylaminocarbonylphenyl)-4-(1-trityl-4-imidazolyl)-1-butanone → HCID 178509866, compound

HRID 22571Notes

Reaction equation

HRID 22571 reaction equation
C([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:42])[CH2:15][CH2:16][CH2:17][C:18]2[N:19]=[CH:20][N:21](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:22]=2)=[CH:10][CH:9]=1)=O)(C)(C)C>S(Cl)(Cl)=O>[C:6]([C:8]1[CH:9]=[CH:10][C:11]([C:14](=[O:42])[CH2:15][CH2:16][CH2:17][C:18]2[N:19]=[CH:20][NH:21][CH:22]=2)=[CH:12][CH:13]=1)#[N:5]

Participants

3

Reactant 1

HCID 543043921-(p-N-tert-butylaminocarbonylphenyl)-4-(1-trityl-4-imidazolyl)-1-butanone

Product 1

HCID 178509866HCID 178509866, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 0.5 g of 1-(p-N-tert-butylaminocarbonylphenyl)-4-(1-trityl-4-imidazolyl)-1-butanone in 20 ml of thionyl chloride is refluxed for 3 h and poured into 100 ml of ice-water. The aqueous phase is extracted with ether (3×20 ml), adjusted to pH=10 and reextracted with methylene chloride. The organic phase is dried and evaporated to yield 1-(p-cyanophenyl)-4-(4-imidazolyl)-1-butanone.

Workup

  1. extractionThe aqueous phase is extracted with ether (3×20 ml)
  2. customThe organic phase is dried
  3. customevaporated

Sources & evidence

ORD record
ord-5c58e8d602dd40afaff18c7e5edb5b77
Source dataset
uspto-grants-1995_06
Patent number
US05428160

Reaction notes

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