Hydrochloric Acid → 2-{2-[3-(3-aminophenyl)ureido]-N-phenylacetamido}-N-methyl-N-phenylacetamide hydrochloride

HRID 1769713Notes

Reaction equation

HRID 1769713 reaction equation
[CH3:1][N:2]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:3](=[O:28])[CH2:4][N:5]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:6](=[O:21])[CH2:7][NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=1)=[O:10].[ClH:35]>C(O)C.C(#N)C.C(OC(C)C)(C)C.C(OC(C)C)(C)C.[Pd]>[ClH:35].[NH2:18][C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[NH:8][CH2:7][C:6]([N:5]([CH2:4][C:3]([N:2]([CH3:1])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:21])[CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 14996988N-methyl-2-{2-[3-(3-nitrophenyl)ureido]-N-phenylacetamido}-N-phenylacetamide

Product 1

HCID 200971412-{2-[3-(3-aminophenyl)ureido]-N-phenylacetamido}-N-methyl-N-phenylacetamide hydrochloride

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 7914Diisopropyl EtherSolventHCID 22714958Acetonitrile diisopropyl etherSolvent

Procedure

0.3 g of 5% palladium-on-charcoal is added to a solution of 1.8 g of N-methyl-2-{2-[3-(3-nitrophenyl)ureido]-N-phenylacetamido}-N-phenylacetamide in 100 cm3 of ethanol. The suspension obtained is stirred for 2 hours at a temperature close to 50° C under a hydrogen atmosphere (100 kPa). After cooling, the catalyst is separated off by filtration and the solution is concentrated to dryness under reduced pressure (2.7 kPa) at 35° C. The residue obtained is dissolved in 60 cm3 of an acetonitrile/diisopropyl ether mixture (20/80 by volume) and 5 cm3 of a 3.5N solution of hydrochloric acid in diisopropyl ether are added. The insoluble product formed is separated off by filtration, air-dried and recrystallization from ethanol. 0.9 g of 2-{2-[3-(3-aminophenyl)ureido]-N-phenylacetamido}-N-methyl-N-phenylacetamide hydrochloride melting at 220° C is thus obtained.

Workup

  1. customThe suspension obtained
  2. customclose to 50° C under a hydrogen atmosphere (100 kPa)
  3. temperatureAfter cooling
  4. customthe catalyst is separated off by filtration
  5. concentrationthe solution is concentrated to dryness under reduced pressure (2.7 kPa) at 35° C
  6. customThe residue obtained
  7. customThe insoluble product formed
  8. customis separated off by filtration
  9. customair-dried
  10. customrecrystallization from ethanol

Sources & evidence

ORD record
ord-e3188a54e6da4e7fad153d501afc00b9
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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