4,4'-Bis(bromomethyl)benzophenone → 3,5-Dimethyl-2-[4-[4-[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thiomethyl]benzoyl]benzylthio]-4(3H)-quinazolinone

HRID 1291332Notes

Reaction equation

HRID 1291332 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]([CH3:43])[CH2:35][CH2:36][N:37]1[C:41]([SH:42])=[N:40][N:39]=[N:38]1.[OH-].[Na+].O>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:42][C:41]3[N:37]([CH2:36][CH2:35][N:34]([CH3:43])[CH3:33])[N:38]=[N:39][N:40]=3)=[CH:25][CH:24]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 23039244,4'-Bis(bromomethyl)benzophenoneHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178424003HCID 178424003, compoundHCID 178483731HCID 178483731, compound

Product 1

HCID 189191243,5-Dimethyl-2-[4-[4-[[1-(2-dimethylaminoethyl)-1H-tetrazol-5-yl]thiomethyl]benzoyl]benzylthio]-4(3H)-quinazolinoneYield 12.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (20 ml) were dissolved 3,5-dimethyl-2-mercapto-4(3H)-quinazolinone (1.03 g), 4,4'-bis(bromomethyl) benzophenone (1.75 g), 1-(2-dimethylaminoethyl)-5-mercapto-1H-tetrazole (865 mg), and 1N-sodium hydroxide/water (11 ml) and the solution 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 (337 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-4c745e32a534440bb903e7a225758e9a
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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