Dimethylformamide → HCID 18919166, compound

HRID 1291341Notes

Reaction equation

HRID 1291341 reaction equation
[SH:1][C:2]1[N:11]([CH3:12])[C:10](=[O:13])[C:9]2[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=2[N:3]=1.[Cl:14][C:15]1[CH:30]=[CH:29][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=2)=[O:20])=[CH:17][CH:16]=1.[OH-].[Na+].O.CN(C=O)C>C(O)C>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([C:19]([C:21]2[CH:28]=[CH:27][C:24]([CH2:25][S:1][C:2]3[N:11]([CH3:12])[C:10](=[O:13])[C:9]4[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=4[N:3]=3)=[CH:23][CH:22]=2)=[O:20])=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178481662HCID 178481662, compound

Product 1

HCID 18919166HCID 18919166, compoundYield 60.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-mercapto-3-methyl-5,6,7,8-tetrahydro-4(3H)-quinazolinone (980 mg), 4-(4-chlorobenzoyl) benzyl bromide (1.53 g), and 1N-sodium hydroxide/water (5.5 ml) in ethanol (10 ml)-DMF (5 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 recrystallized from methanol-ethyl acetate to provide the title compound as colorless solid (1.27 g).

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 recrystallized from methanol-ethyl acetate

Sources & evidence

ORD record
ord-4cbf1db576d9473e9542cfdca0234ec5
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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