Sodium Carbonate → HCID 85436904, compound

HRID 1605251Notes

Reaction equation

HRID 1605251 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([NH:13][CH2:14][C:15]3[CH:23]=[CH:22][C:21]4[O:20][CH2:19][O:18][C:17]=4[CH:16]=3)[N:10]=[C:9]([S:24][CH2:25][C:26]#[N:27])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:29][OH:30].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[O:20]1[C:21]2[CH:22]=[CH:23][C:15]([CH2:14][NH:13][C:11]3[CH:12]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[C:9]([S:24][CH2:25][C:26](=[N:29][OH:30])[NH2:27])[N:10]=3)=[CH:16][C:17]=2[O:18][CH2:19]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 12228978HCID 12228978, compound

Product 1

HCID 85436904HCID 85436904, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 11.20 g. (0.03 mole) of [4-phenyl-6-(piperonylamino)-2-pyrimidinylthio]acetonitrile, 4.14 g. (0.06 mole) of hydroxylamine hydrochloride and 12.70 g. (0.12 mole) of sodium carbonate in 200 ml of N,N-dimethylformamide was heated on a steam bath for four 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 left at room temperature overnight. The precipitate which formed was collected and recrystallized from a mixture of ethyl acetate-petroleum ether to give 4.8 g. of product, mp. 160°-163°.

Workup

  1. additionA mixture of 11.20 g
  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. customThe precipitate which formed
  7. customwas collected
  8. customrecrystallized from a mixture of ethyl acetate-petroleum ether
  9. customto give 4.8 g

Sources & evidence

ORD record
ord-a4b495151df647af84b4a00d865034f6
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

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