P-Anisidine → Acetonitrile, [[4-[(4-methoxyphenyl)amino]-6-methyl-2-pyrimidinyl]thio]-

HRID 1605242Notes

Reaction equation

HRID 1605242 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH2:10][C:11]#[N:12])[N:3]=1.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][CH2:10][C:11]#[N:12])[N:3]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 10340Sodium CarbonateHCID 12228966Acetonitrile, [(4-chloro-6-methyl-2-pyrimidinyl)thio]-

Product 1

HCID 12228969Acetonitrile, [[4-[(4-methoxyphenyl)amino]-6-methyl-2-pyrimidinyl]thio]-

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 15.0 g. (0.075 mole) of (4-chloro-6methyl-2-pyrimidinylthio)aceto nitrile, 10.0g. (0.075 mole) p-anisidine and 7.5 g. (0.075 mole) of sodium carbonate in 150 ml of ethanol was heated under reflux for five hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The oily residue was dissolved in ethyl acetate. Dilution of the ethyl acetate solution with petroleum ether and cooling in ice yielded a precipitate. This solid was collected and recrystallized from a mixture of benzene-petroleum ether to afford 7.2 g. of product, m.p. 128°-131°.

Workup

  1. additionA stirred mixture of 15.0 g
  2. temperatureunder reflux for five hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in a rotary evaporator
  5. dissolutionThe oily residue was dissolved in ethyl acetate
  6. temperatureDilution of the ethyl acetate solution with petroleum ether and cooling in ice
  7. customyielded a precipitate
  8. customThis solid was collected
  9. customrecrystallized from a mixture of benzene-petroleum ether
  10. customto afford 7.2 g

Sources & evidence

ORD record
ord-e29539e88d2246e2adbe451d183be3ad
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

Loading…