Water → HCID 14575153, compound

HRID 1085055Notes

Reaction equation

HRID 1085055 reaction equation
C[O-].[Na+].Cl.Cl[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH2:13]([N:17]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]1[SH:28])[CH:14]([CH3:16])[CH3:15].O>CO>[CH2:13]([N:17]1[C:26](=[O:27])[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=[C:18]1[S:28][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)[CH:14]([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 23392Picolyl chloride hydrochlorideHCID 10942334Sodium MethoxideHCID 178448727HCID 178448727, compound

Product 1

HCID 14575153HCID 14575153, compoundYield 46.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.4 ml Of 28% methanolic solution of sodium methoxide and 2.3 g of 2-chloromethylpyridine hydrochloride were added, in turn, to a solution of 3.0 g 3-isobutyl-2-mercapto-4(3H)-quinazolinone in 50 ml of methanol, and the stirring was continued at room temperature for 15 hours. The reaction solution was poured into about 300 ml of water and extracted with chloroform. The extract was dried over sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica column chromatography eluted with 10% ethyl acetate in chloroform. The fraction obtained from the eluent was further purified by crystallization from a mixture of ethyl acetate and diisopropylether to give 1.92 g of the title compound.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe extract was dried over sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica column chromatography
  5. washeluted with 10% ethyl acetate in chloroform
  6. customThe fraction obtained from the eluent
  7. customwas further purified by crystallization from a mixture of ethyl acetate and diisopropylether

Sources & evidence

ORD record
ord-43b4cc05b8ed4f8db4b5c713a760d3e2
Source dataset
uspto-grants-1991_04
Patent number
US05008266

Reaction notes

Loading…