Pyridine → HCID 14997002, compound

HRID 1769718Notes

Reaction equation

HRID 1769718 reaction equation
N1C=CC=CC=1.Cl.[NH2:8][OH:9].[CH:10]([C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:42])[NH:20][CH2:21][C:22]([N:24]([CH2:31][C:32]([N:34]([CH3:41])[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:33])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:23])[CH:15]=[CH:16][CH:17]=1)=O>O.CO>[OH:9]/[N:8]=[CH:10]/[C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:42])[NH:20][CH2:21][C:22]([N:24]([CH2:31][C:32]([N:34]([CH3:41])[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:33])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:23])[CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 14997001HCID 14997001, compound

Product 1

HCID 14997002HCID 14997002, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.18 g of pyridine and then 0.17 g of hydroxylamine hydrochloride in solution in 3 cm3 of water are added to a solution of 1 g of 2-{2-[3-(3-formylphenyl)ureido]-N-phenylacetamido}-N-methyl-N-phenylacetamide in 6 cm3 of methanol. The mixture is heated under reflux for 3 hours. After cooling, the insoluble product is separated off by filtration, washed with 3 times 3 cm3 of water and air-dried. After recrystallization from a dimethylformamide/water mixture (50/50 by volume), 0.5 g of (E)-2-{2-[3-(3-hydroxyiminomethylphenyl)ureido]-N-phenylacetamido}-N-methyl-N-phenylacetamide melting at 219° C is obtained.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. customthe insoluble product is separated off by filtration
  5. washwashed with 3 times 3 cm3 of water
  6. customair-dried
  7. customAfter recrystallization from a dimethylformamide/water mixture (50/50 by volume)

Sources & evidence

ORD record
ord-835725b7d0e64814a94cb633ac306423
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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