tert-Butyldimethylsilyl chloride → HCID 19032402, compound

HRID 266071Notes

Reaction equation

HRID 266071 reaction equation
Cl[Si:2]([CH3:8])([CH3:7])[C:3]([CH3:6])([CH3:5])[CH3:4].[Br:9][C:10]1[CH:44]=[CH:43][C:13]([C:14]([CH:16]([N:18]2[C:22](=[O:23])[N:21]([C:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH2:35][CH2:34][N:33]([C:36]5[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=5)[CH2:32][CH2:31]4)=[CH:26][CH:25]=3)[CH:20]=[N:19]2)[CH3:17])=[O:15])=[CH:12][CH:11]=1>ClCCl.N1C=CC=CC=1>[Br:9][C:10]1[CH:44]=[CH:43][C:13]([C:14]([CH:16]([N:18]2[C:22](=[O:23])[N:21]([C:24]3[CH:25]=[CH:26][C:27]([N:30]4[CH2:31][CH2:32][N:33]([C:36]5[CH:41]=[CH:40][C:39]([O:42][Si:2]([C:3]([CH3:6])([CH3:5])[CH3:4])([CH3:8])[CH3:7])=[CH:38][CH:37]=5)[CH2:34][CH2:35]4)=[CH:28][CH:29]=3)[CH:20]=[N:19]2)[CH3:17])=[O:15])=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 15125569HCID 15125569, compound

Product 1

HCID 19032402HCID 19032402, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(chlorodimethylsilyl)-2-methylpropane (0.011 mol) in dichloromethane (20 ml) was added to a stirred solution of 2-[1-(4-bromobenzoyl)ethyl]-2,4-dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3H-1,2,4-triazol-3-one (0.009 mol) in pyridine (20 ml) under a nitrogen atmosphere. Stirring was continued for 1 week at room temperature. The reaction mixture was evaporated and the residue was dissolved in dichloromethane. This solution was purified over silica gel on a glass filter (eluent: dichloromethane). The pure fractions were collected and the solvent was evaporated. The residue (3.5 g) was recrystallized from ethyl acetate. The product was filtered off and dried, yielding 2.7 g (45 %) of 2-[1-(4-bromobenzoyl)ethyl]-4-[4-[4-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one; mp. 177.8° C. (comp. 47).

Workup

  1. waitwas continued for 1 week at room temperature
  2. customThe reaction mixture was evaporated
  3. dissolutionthe residue was dissolved in dichloromethane
  4. customThis solution was purified over silica gel on a glass
  5. filtrationfilter (eluent: dichloromethane)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue (3.5 g) was recrystallized from ethyl acetate
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-d5c9ae91f5e24190bd25b13399762a99
Source dataset
uspto-grants-1997_07
Patent number
US05650411

Reaction notes

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