Sodium Carbonate → HCID 12228981, compound

HRID 1605244Notes

Reaction equation

HRID 1605244 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([S:11][CH2:12][C:13]#[N:14])[N:3]=1.[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH2:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][NH:21][C:2]2[CH:7]=[C:6]([CH2:8][CH2:9][CH3:10])[N:5]=[C:4]([S:11][CH2:12][C:13]#[N:14])[N:3]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 660364-ChlorobenzylamineHCID 12228980Acetonitrile, [(4-chloro-6-propyl-2-pyrimidinyl)thio]-

Product 1

HCID 12228981HCID 12228981, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of 13.62 g. (0.06 mole) of (4-chloro-6-propyl-2-pyrimidinylthio)acetonitrile, 8.40 g. (0.06 mole) of p-chlorobenzylamine and 6.36 g. (0.06 mole) of sodium carbonate was heated under reflux in 150 ml of ethanol for five hours. The mixture was filtered and the filtrate was evaporated in a rotary evaportor. The residue was dissolved in ether (150 ml) and extracted with 150 ml of 10% concentrated hydrochloric acid solution. The ether layer was dried over magnesium sulfate, filtered and evaporated in a rotary evaporator. This residue was dissolved in benzene, diluted with a little heptane and was cooled in ice. The precipitate which formed was collected and recrystallized a second time from a benzene-heptane mixture to give 3.6 g. of product, m.p. 68°-70°.

Workup

  1. additionA stirred suspension of 13.62 g
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in a rotary evaportor
  4. dissolutionThe residue was dissolved in ether (150 ml)
  5. extractionextracted with 150 ml of 10% concentrated hydrochloric acid solution
  6. dry with materialThe ether layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in a rotary evaporator
  9. dissolutionThis residue was dissolved in benzene
  10. additiondiluted with a little heptane
  11. temperaturewas cooled in ice
  12. customThe precipitate which formed
  13. customwas collected
  14. customrecrystallized a second time from a benzene-heptane mixture
  15. customto give 3.6 g

Sources & evidence

ORD record
ord-3504b08575e447919804a58a8b230c51
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

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