Sodium Carbonate → HCID 54392575, compound

HRID 1605250Notes

Reaction equation

HRID 1605250 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[C:12]([CH2:14][CH2:15][CH3:16])[N:11]=[C:10]([S:17][CH2:18][C:19]#[N:20])[N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[C:12]([CH2:14][CH2:15][CH3:16])[N:11]=[C:10]([S:17][CH2:18][C:19](=[N:24][OH:25])[NH2:20])[N:9]=2)=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 12228981HCID 12228981, compound

Product 1

HCID 54392575HCID 54392575, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.60 g. (0.02 mole) of [4-(p-chlorobenzylamino)-6-propyl-2-pyrimidinylthio]acetonitrile, 2.76 g. (0.04 mole) of hydroxylamine hydrochloride and 8.48 g. (0.08 mole) of sodium carbonate in 100 ml of N,N-dimethylformamide was heated on a steam bath for three and one-half hours. The mixture was filtered, diluted with 250 ml of water and extracted with 100 ml of ether. The ether layer was dried over magnesium sulfate, filtered and evaporated in a rotary evaporator. The residue was dissolved in ethanol, diluted with petroleum ether and cooled in ice. The precipitate which formed was collected and recrystallized from a mixture of ethanol-petroleum ether to give the analytical sample, m.p. 50° dec.

Workup

  1. additionA mixture of 6.60 g
  2. filtrationThe mixture was filtered
  3. additiondiluted with 250 ml of water
  4. extractionextracted with 100 ml of ether
  5. dry with materialThe ether layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in a rotary evaporator
  8. dissolutionThe residue was dissolved in ethanol
  9. additiondiluted with petroleum ether
  10. temperaturecooled in ice
  11. customThe precipitate which formed
  12. customwas collected
  13. customrecrystallized from a mixture of ethanol-petroleum ether
  14. customto give the analytical sample, m.p. 50° dec.

Sources & evidence

ORD record
ord-1576a1ab33314b21968753c3098a7f42
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

Loading…