Potassium Carbonate → HCID 18919138, compound

HRID 1291369Notes

Reaction equation

HRID 1291369 reaction equation
[OH:1][C:2]1[CH:30]=[CH:29][C:5]([C:6]([C:8]2[CH:28]=[CH:27][C:11]([CH2:12][S:13][C:14]3[N:23]([CH3:24])[C:22](=[O:25])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][C:20]=4[CH3:26])[N:15]=3)=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36][Cl:37].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[ClH:37].[CH3:24][N:23]1[C:22](=[O:25])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:26])[N:15]=[C:14]1[S:13][CH2:12][C:11]1[CH:27]=[CH:28][C:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([O:1][CH2:36][CH2:35][CH2:34][N:33]([CH3:38])[CH3:32])=[CH:30][CH:29]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 943083-(Dimethylamino)propyl chloride hydrochlorideHCID 189188882-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone

Product 1

HCID 18919138HCID 18919138, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[4-(4-hydroxybenzoyl)benzylthio]-3,5-dimethyl-4(3H)-quinazolinone (311 mg), 3-dimethylaminopropyl chloride hydrochloride (249 mg) and potassium carbonate (322 mg) in DMF (5 ml) was stirred at 60° C. for 18 hours. This reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, and dried. Then, hydrogen chloride/ethyl acetate was added and the precipitated hydrochloride was collected by filtration to provide the title compound as colorless solid (185 mg).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customdried
  5. additionThen, hydrogen chloride/ethyl acetate was added
  6. filtrationthe precipitated hydrochloride was collected by filtration

Sources & evidence

ORD record
ord-16b6bdf3660843249628af8d08c1b184
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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