2-Butyl-6-(1-hydroxyethyl)-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-4(3H)-quinazolinone → HCID 178441465, compound

HRID 486031Notes

Reaction equation

HRID 486031 reaction equation
[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[N:32](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:31]=[N:30][N:29]=3)=[CH:18][CH:17]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:53]([OH:55])[CH3:54])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]>CC(C)=O.O.Cl>[CH2:1]([C:5]1[N:14]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[NH:29][N:30]=[N:31][N:32]=3)=[CH:20][CH:21]=2)[C:13](=[O:52])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH:53]([OH:55])[CH3:54])[CH:11]=2)[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 200793502-Butyl-6-(1-hydroxyethyl)-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-4(3H)-quinazolinone

Product 1

HCID 178441465HCID 178441465, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a suspension of 2.00 g of 2-butyl-6-(1-hydroxyethyl)-3-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'biphenyl]-4-yl]methyl]-4(3H)-quinazolinone in 70 ml of 3:1 acetone-water is added one drop of 5% aqueous hydrochloric acid solution. The mixture is then heated at reflux for 16 hours. After cooling, the reaction mixture is concentrated in vacuo and the residue purified by flash chromatography on silica gel by elution with 9:1 chloroform-methanol to afford 0.915 g of the desired product as a white solid, m.p. 146°-147° C.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureat reflux for 16 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture is concentrated in vacuo
  5. customthe residue purified by flash chromatography on silica gel by elution with 9:1 chloroform-methanol

Sources & evidence

ORD record
ord-09b42366cc4f4003bf58f08c836eaad2
Source dataset
uspto-grants-1994_03
Patent number
US05290780

Reaction notes

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