4,4'-Bis(bromomethyl)benzophenone → HCID 18919129, compound

HRID 1291334Notes

Reaction equation

HRID 1291334 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.[SH:33][C:34]1[S:35][CH2:36][CH2:37][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:33][CH:34]3[NH:38][CH2:37][CH2:36][S:35]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 178527880HCID 178527880, compound

Product 1

HCID 18919129HCID 18919129, compoundYield 19.3%

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), 2-mercaptothiazoline (600 mg), and 1N-sodium hydroxide/water (11 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 (hexane: ethyl acetate: chloroform=3:1:1) and crystallized from methanol to provide the title compound as colorless solid (489 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 (hexane: ethyl acetate: chloroform=3:1:1)
  7. customcrystallized from methanol

Sources & evidence

ORD record
ord-12a2b9ee99fc472e9bda02b0a8b8ffe4
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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