3-Thiocresol → 1-(3-Tolylsulfenyl)methyl-5-chloropyrimidin-2-one

HRID 247084

Reaction equation

HRID 247084 reaction equation
Cl[CH2:2][N:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[N:5][C:4]1=[O:10].[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([SH:18])[CH:13]=1.C(N(CC)CC)C>>[C:12]1([CH3:11])[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH2:2][N:3]2[CH:8]=[C:7]([Cl:9])[CH:6]=[N:5][C:4]2=[O:10])[CH:13]=1

Participants

4

Reactant 3

HCID 79303-ThiocresolHCID 8471TriethylamineHCID 201613341-Chloromethyl-5-chloropyrimidin-2-one

Product 1

HCID 135300961-(3-Tolylsulfenyl)methyl-5-chloropyrimidin-2-one

Conditions

Temperature
40 °C

Procedure

1-Chloromethyl-5-chloropyrimidin-2-one (see Preparation 15) (1.0 mmol) was added to a mixture of m-thiocresol (1.0 mmol) and triethylamine (1.0 mmol). The mixture was stirred at room temperature for 20 mins and at 40° C. for 20 mins before the solvent was distilled off and the residue triturated with water, extracted into chloroform, dried (MgSO4) and evaporated. The residue was washed with cold acetone (1 ml). The insoluble product was identical with an authentic sample prepared as described in Example 14. Yield: 60 mg, 22%.

Workup

  1. distillationwas distilled off
  2. customthe residue triturated with water
  3. extractionextracted into chloroform
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. washThe residue was washed with cold acetone (1 ml)
  7. customprepared

Sources & evidence

ORD record
ord-406721d3280f4895bc58b724e66e5d4b
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Linked notes

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