Dimethyl Sulfide → HCID 12235381, compound

HRID 363976Notes

Reaction equation

HRID 363976 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][S:11][CH3:12].ClN1C(=O)CCC1=O>C(Cl)Cl>[CH3:10][S:11]([CH3:12])=[N:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 130212-Amino-4,6-dimethyl pyrimidineHCID 31398Chlorosuccinimide

Product 1

HCID 12235381HCID 12235381, compoundYield 21.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 12.3 g (0.10 mole) of 2-amino-4,6-dimethylpyrimidine and 8 ml (0.109 mole) of methylsulfide in 100 ml of methylene chloride at -20° C. was added dropwise a solution of 13.3 g (0.10 mole) of N-chlorosuccinimide in 300 ml of methylene chloride. After addition, the resulting solution was warmed to room temperature and was kept at room temperature for one hour with stirring. The solution was then washed with 400 ml of 2.5% sodium hydroxide aqueous solution and then 400 ml of water. This solution was dried over sodium sulfate and filtered. The filtrate was washed with ethyl ether, and dried under vacuum at ambient temperature to afford 4 g of the title compound as a white solid, m.p. 117°-120° C.

Workup

  1. additionAfter addition
  2. washThe solution was then washed with 400 ml of 2.5% sodium hydroxide aqueous solution
  3. dry with materialThis solution was dried over sodium sulfate
  4. filtrationfiltered
  5. washThe filtrate was washed with ethyl ether
  6. customdried under vacuum at ambient temperature

Sources & evidence

ORD record
ord-6fa8d64d87e34491beb524dedd0d52a2
Source dataset
uspto-grants-1986_08
Patent number
US04604133

Reaction notes

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