Sodium Hydroxide → 3,5-Dimethyl-2-[4-[4-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]benzoyl]benzylthio]-4(3H)-quinazolinone

HRID 1291335Notes

Reaction equation

HRID 1291335 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[SH:14].Br[CH2:16][C:17]1[CH:32]=[CH:31][C:20]([C:21]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29]Br)=[CH:25][CH:24]=2)=[O:22])=[CH:19][CH:18]=1.[CH3:33][N:34]1[C:38]([SH:39])=[N:37][N:36]=[N:35]1.[OH-].[Na+]>CN(C=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[S:14][CH2:16][C:17]1[CH:32]=[CH:31][C:20]([C:21](=[O:22])[C:23]2[CH:28]=[CH:27][C:26]([CH2:29][S:39][C:38]3[N:34]([CH3:33])[N:35]=[N:36][N:37]=3)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 23039244,4'-Bis(bromomethyl)benzophenoneHCID 178424003HCID 178424003, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 189192953,5-Dimethyl-2-[4-[4-[(1-methyl-1H-tetrazol-5-yl)thiomethyl]benzoyl]benzylthio]-4(3H)-quinazolinoneYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-dimethyl-2-mercapto-4(3H)-quinazolinone (1.03 g), 4,4'-bis (bromomethyl)benzophenone (1.75 g), 1-methyl-5-mercapto-1H-tetrazole (700 mg), and 1N-aqeuous sodium hydroxide solution (5.5 ml) in DMF (20 ml) was stirred at room temperature for 30 minutes. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, dried, and concentrated. The residue was purified by silica gel column chromatography (chloroform: methanol: aqueous ammonia=50:1:0.1) and crystallized from methanol to provide the title compound as colorless solid (603 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (chloroform: methanol: aqueous ammonia=50:1:0.1)
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-e644a2034e254fe1b2cd3c1b468bab7c
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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