Sodium Carbonate → 2-[4-(p-Methoxyphenylamino)-6-Methyl-2-Pyrimidinylthio]Acetamidoxime

HRID 1605249Notes

Reaction equation

HRID 1605249 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([S:17][CH2:18][C:19]#[N:20])[N:11]=2)=[CH:5][CH:4]=1.Cl.[NH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10]2[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([S:17][CH2:18][C:19](=[N:22][OH:23])[NH2:20])[N:11]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 12228969Acetonitrile, [[4-[(4-methoxyphenyl)amino]-6-methyl-2-pyrimidinyl]thio]-

Product 1

HCID 544689002-[4-(p-Methoxyphenylamino)-6-Methyl-2-Pyrimidinylthio]AcetamidoximeYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 11.20 g (0.04 mole) of [4-(p-anisidino)-6-methyl-2-pyrimidinylthio]acetonitrile, 5.52 g (0.08 mole) of hydroxylamine hydrochloride and 16.90 g (0.16 mole) of sodium carbonate in 150 ml of N,N-dimethylformamide was heated on a steam bath for three and one-half hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was dissolved in ethyl acetate, diluted with petroleum ether and was cooled in ice. The precipitate which formed was collected and recrystallized from a mixture of ethanol-petroleum ether to afford 3.7 g of product, m.p. 189°-191° d.

Workup

  1. temperaturewas heated on a steam bath for three and one-half hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in a rotary evaporator
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. additiondiluted with petroleum ether
  6. temperaturewas cooled in ice
  7. customThe precipitate which formed
  8. customwas collected
  9. customrecrystallized from a mixture of ethanol-petroleum ether

Sources & evidence

ORD record
ord-e7a470293e50434d96f15ae6c922ba84
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

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