Dimethyl Disulfide → HCID 18662974, compound

HRID 1956177Notes

Reaction equation

HRID 1956177 reaction equation
N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]([CH3:20])([CH3:19])[CH:8]2[C:11]2[C:12]([S:17][CH3:18])=[N:13][CH:14]=[N:15][CH:16]=2)=[CH:4][CH:3]=1.F[B-](F)(F)F.N#[O+].[CH3:28][S:29]SC.C[S-].[Na+]>C(#N)C.CCOCC>[CH3:19][C:7]1([CH3:20])[CH2:6][C:5]2[C:9](=[CH:10][C:2]([S:29][CH3:28])=[CH:3][CH:4]=2)[CH:8]1[C:11]1[C:12]([S:17][CH3:18])=[N:13][CH:14]=[N:15][CH:16]=1

Participants

7

Reactant 4

HCID 12232Dimethyl DisulfideHCID 4378561Sodium methanethiolateHCID 11137142Nitrilooxonium tetrafluoroborateHCID 18662979HCID 18662979, compound

Product 1

HCID 18662974HCID 18662974, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

To a mixture of 1.0 g (3.5 mmol) of 5-(6-amino-2,2-dimethylindan-1-yl)-4-methylthiopyrimidine in 25 mL of dry acetonitrile at 5° C. was added with stirring 1.0 g (7.0 mmol) of nitrosonium tetrafluoroborate. After 30 min the resulting solution was poured with stirring into a solution of 20 g (0.20 mol) of dimethyl disulfide in 100 mL of acetonitrile. After 2 hr, 0.50 g of sodium methanethiolate was added and the reaction mixture was heated with stirring to 60° C. for 16 hr. The mixture was cooled and poured into 600 mL of ether with stirring. The ethereal phase was recovered and was washed with water (2×100 mL), dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel to obtain 500 mg (45 percent of theory) of the title compound as a light gold oil.

Workup

  1. additionwas added
  2. additionAfter 30 min the resulting solution was poured
  3. temperaturethe reaction mixture was heated
  4. temperatureThe mixture was cooled
  5. stirringwith stirring
  6. customThe ethereal phase was recovered
  7. washwas washed with water (2×100 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated by evaporation under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-1516747364bb455aa901bcdffe44c4e5
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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