HCID 13188003, compound → HCID 13188004, compound

HRID 544552Notes

Reaction equation

HRID 544552 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[Na+].Br[CH2:7][C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:16](=[O:25])[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:14]=2[CH3:26])[N:9]=1>CN(C)C=O>[C:1]([S:3][CH2:7][C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[C:16](=[O:25])[C:15]2[C:10](=[CH:11][C:12]([CH3:32])=[C:13]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:14]=2[CH3:26])[N:9]=1)(=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 13188003HCID 13188003, compoundHCID 23700354HCID 23700354, compound

Product 1

HCID 13188004HCID 13188004, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium thioacetate (235 mg) was added to an ice-cooled, stirred solution of 1 g of 2-bromomethyl-3-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-4(3H)-quinazolinone in 4 ml of dimethylformamide. After stirring for an additional 30 minutes, the mixture was poured into ice-water. The resulting precipitate was filtered off, washed with water, and dried in vacuo. The crude product was chromatographed on a column of silica gel using 5% ethyl acetate in benzene as an eluent to give 619 mg (yield, 62.5%) of 2-(acetylmercaptomethyl)-3-(2-chlorophenyl)-6-ethoxycarbonyl-5,7-dimethyl-4(3H)-quinazolinone melting at 103°-105° C. (recrystallized from methanol).

Workup

  1. temperaturecooled
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with water
  4. customdried in vacuo
  5. customThe crude product was chromatographed on a column of silica gel using 5% ethyl acetate in benzene as an eluent

Sources & evidence

ORD record
ord-149e9442b0304b8d9a0a5dc1d119ef4d
Source dataset
uspto-grants-1984_05
Patent number
US04451467

Reaction notes

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