Nitric Acid → HCID 18662975, compound

HRID 1956175Notes

Reaction equation

HRID 1956175 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[C:11]1[C:12]([S:17][CH3:18])=[N:13][CH:14]=[N:15][CH:16]=1.[N+:20]([O-])([OH:22])=[O:21].C(=O)([O-])[O-].[K+].[K+]>ClCCl>[CH3:1][C:2]1([CH3:19])[CH2:10][C:9]2[C:4](=[CH:5][C:6]([N+:20]([O-:22])=[O:21])=[CH:7][CH:8]=2)[CH:3]1[C:11]1[C:12]([S:17][CH3:18])=[N:13][CH:14]=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 232269825-(2,2-Dimethyl-2,3-dihydro-1H-inden-1-yl)-4-(methylsulfanyl)pyrimidine

Product 1

HCID 18662975HCID 18662975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30 g (0.11 mol) of 5-(2,2-dimethylindan-1-yl)-4-methylthiopyrimidine in 500 mL of dichloromethane was added dropwise 100 mL of 90 percent nitric acid. After 1 hr the reaction mixture was poured onto a large volume of ice. The mixture was slowly neutralized with solid potassium carbonate and was then extracted with ether. The organic phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain 36 g of a tan solid. This was recrystallized from 400 mL of ethyl acetate to obtain 12 g of the title compound as a white solid melting at 167°-168° C.

Workup

  1. additionAfter 1 hr the reaction mixture was poured onto a large volume of ice
  2. extractionwas then extracted with ether
  3. customThe organic phase was recovered
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-099f140587bc41a49f2af5275c73cb3e
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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