Sodium Carbonate → [4-(p-Chlorobenzylamino)-6-methyl-2-Pyrimidinylthio]Acetonitrile

HRID 1605241Notes

Reaction equation

HRID 1605241 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.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH2:19])=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][NH:19][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:16][CH:15]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 660364-ChlorobenzylamineHCID 12228966Acetonitrile, [(4-chloro-6-methyl-2-pyrimidinyl)thio]-

Product 1

HCID 12228967[4-(p-Chlorobenzylamino)-6-methyl-2-Pyrimidinylthio]Acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 5.97 g. (0.03 mole) of (4-chloro-6-methyl-2-pyrimidinylthio)acetonitrile, 4.2 g. (0.03 mole) of 4-chlorobenzylamine and 3.15 g. (0.03 mole) of sodium carbonate in 150 ml of absolute ethanol was heated under reflux for 6 hours. The mixture was filtered and the filtrate evaporated in a rotary evaporator. The residue was triturated with petroleum ether containing a little ethanol. The solid which crystallized was collected and recrystallized from ethyl acetate with petroleum ether added to induce precipitation affording 3.2 g. of product, m.p. 99°-101°.

Workup

  1. additionA stirred mixture of 5.97 g
  2. temperatureunder reflux for 6 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated in a rotary evaporator
  5. customThe residue was triturated with petroleum ether containing a little ethanol
  6. customThe solid which crystallized
  7. customwas collected
  8. customrecrystallized from ethyl acetate with petroleum ether
  9. additionadded
  10. customprecipitation
  11. customaffording 3.2 g

Sources & evidence

ORD record
ord-bc8795817c86473cb84898099f4dc022
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

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