O-methylhydroxylammonium chloride → HCID 20097088, compound

HRID 1769717Notes

Reaction equation

HRID 1769717 reaction equation
[CH3:1][O:2][NH3+:3].[Cl-].[C:5]([C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:38])[NH:16][CH2:17][C:18]([N:20]([CH2:27][C:28]([N:30]([CH3:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:29])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[CH:11]=[CH:12][CH:13]=1)(=O)[CH3:6]>O.C(O)C>[CH3:1][O:2]/[N:3]=[C:5](\[C:8]1[CH:9]=[C:10]([NH:14][C:15](=[O:38])[NH:16][CH2:17][C:18]([N:20]([CH2:27][C:28]([N:30]([CH3:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:29])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:19])[CH:11]=[CH:12][CH:13]=1)/[CH3:6]

Participants

5

Reactant 2

HCID 11639O-methylhydroxylammonium chlorideHCID 14996996HCID 14996996, compound

Product 1

HCID 20097088HCID 20097088, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.16 g of 0-methylhydroxylamine hydrochloride in solution in 2 cm3 of water is added to a solution of 0.92 g of 2-{2-[3-(3-acetylphenyl)ureido]-N-phenylacetamido}-N-methyl-N-phenylacetamide in 10 cm3 of ethanol. The mixture is stirred under reflux for 3 hours and then at a temperature close to 25° C for 12 hours and concentrated to a volume of about 3 cm3 under reduced pressure (2.7 kPa) at 40° C. 20 cm3 of distilled water are then added and the insoluble product is separated off by filtration and air-dried. After recrystallization from a methanol/diisopropyl ether mixture (60/40 by volume), 0.31 g of (Z)-2-{2-{3-[3-(1-methoxyiminoethyl)phenyl]ureido}-N-phenylacetamido}-N-methyl-N-phenylacetamide melting at 165° C is obtained.

Workup

  1. temperatureunder reflux for 3 hours
  2. customat a temperature close to 25° C for 12 hours
  3. concentrationconcentrated to a volume of about 3 cm3 under reduced pressure (2.7 kPa) at 40° C
  4. addition20 cm3 of distilled water are then added
  5. customthe insoluble product is separated off by filtration
  6. customair-dried
  7. customAfter recrystallization from a methanol/diisopropyl ether mixture (60/40 by volume)

Sources & evidence

ORD record
ord-01c881882cb34cc189829e8e85b02384
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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