Hydrochloric Acid → 2-[4-(p-Chlorbenzylamino)-6-Methyl-2-Pyrimidinylthio]Acetamidoxime

HRID 1605247Notes

Reaction equation

HRID 1605247 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([S:15][CH2:16][C:17]#[N:18])[N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:22][OH:23].C(=O)([O-])[O-].[Na+].[Na+].Cl>CN(C)C=O.C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]2[CH:13]=[C:12]([CH3:14])[N:11]=[C:10]([S:15][CH2:16][C:17](=[N:22][OH:23])[NH2:18])[N:9]=2)=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 12228967[4-(p-Chlorobenzylamino)-6-methyl-2-Pyrimidinylthio]Acetonitrile

Product 1

HCID 545119502-[4-(p-Chlorbenzylamino)-6-Methyl-2-Pyrimidinylthio]Acetamidoxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.6g. (0.035 mole) of [4-(p-chlorobenzylamino)-6-methyl-2-pyrimidinylthio]acetonitrile, 4.83 g. (0.07 mole) of hydroxylamine hydrochloride and 14.7 g. (0.14 mole) of sodium carbonate in 100 ml of N,N-dimethylformamide was heated on a steam bath for 3 hours. The mixture was filtered and the filtrate evaporated in a rotary-evaporator. The residue was triturated with petroleum ether containing a little ethyl acetate. The solid which crystallized was collected and recrystallized from ethyl acetate to give pure free base, m.p. 113°-116°. This free base was dissolved in absolute ethanol and acidified with an ethereal hydrochloric acid solution to give 3.5 g. of product, as the dihydrochloric salt, m.p. 230°-232° d.

Workup

  1. additionA mixture of 10.6g
  2. filtrationThe mixture was filtered
  3. customthe filtrate evaporated in a rotary-evaporator
  4. customThe residue was triturated with petroleum ether containing a little ethyl acetate
  5. customThe solid which crystallized
  6. customwas collected
  7. customrecrystallized from ethyl acetate
  8. customto give pure free base, m.p. 113°-116°
  9. customto give 3.5 g

Sources & evidence

ORD record
ord-abdb051e69f74fad84db5afa1229849c
Source dataset
uspto-grants-1976_04
Patent number
US03950339

Reaction notes

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