Sodium Carbonate → 2-[4-(1,3-Benzodioxol-4-Ylmethylamino)-6-Methyl-2-Pyrimidinylthio]Acetamidoxime

HRID 1605248Notes

Reaction equation

HRID 1605248 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:18]=[CH:17][C:16]3[O:15][CH2:14][O:13][C:12]=3[CH:11]=2)[N:5]=[C:4]([S:19][CH2:20][C:21]#[N:22])[N:3]=1.Cl.[NH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[O:13]1[C:12]2[CH:16]=[CH:17][CH:18]=[C:10]([CH2:9][NH:8][C:6]3[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([S:19][CH2:20][C:21](=[N:24][OH:25])[NH2:22])[N:5]=3)[C:11]=2[O:15][CH2:14]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 12228971(4-Methyl-6-piperonylamino-2-pyrimidinylthio)acetonitrile

Product 1

HCID 867332212-[4-(1,3-Benzodioxol-4-Ylmethylamino)-6-Methyl-2-Pyrimidinylthio]Acetamidoxime

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.20 g. (0.02 mole) of (4-methyl-6-piperonylamino-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 four hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was triturated with ether and the insoluble material was collected and recrystallized from a mixture of ethanol-N,N-dimethylacetamide to give 3.5 g. of product, m.p. 190°-192° dec.

Workup

  1. additionA mixture of 6.20 g
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated in a rotary evaporator
  4. customThe residue was triturated with ether
  5. customthe insoluble material was collected
  6. customrecrystallized from a mixture of ethanol-N,N-dimethylacetamide
  7. customto give 3.5 g

Sources & evidence

ORD record
ord-074e8324a4e7496eafd83fca1b4194e3
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

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