Triethylamine → 2-{[(4-Nitrophenyl)methyl]amino}propanediamide

HRID 358143Notes

Reaction equation

HRID 358143 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH:13]([C:17]([NH2:19])=[O:18])[C:14]([NH2:16])=[O:15].C(N(CC)CC)C>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][CH:13]([C:17]([NH2:19])=[O:18])[C:14]([NH2:16])=[O:15])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 291474-NitrobenzylamineHCID 132716282-Bromopropanediamide

Product 1

HCID 132716292-{[(4-Nitrophenyl)methyl]amino}propanediamideYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 41.60 g of p-nitrobenzylamine in 660 ml of dry ethanol was added 49.34 g of α-bromomalonamide and 38.2 ml of triethylamine. After being stirred for two hours under refluxing, the reaction mixture was cooled to room temperature. And then separated crystals were filtered off, washed with ethanol and isopropyl ether, and dried to give 53.36 g of α-(4-nitrobenzyl)aminomalonamide. And a mixture of 50.45 g of α-(4-nitrobenzyl)aminomalonamide, 177.8 g of triethyl orthoformate and 0.76 g of p-toluenesulfonic acid monohydrate in 1.3 liters of dry ethanol was stirred for three hours under refluxing in an argon atmosphere. The reaction mixture was cooled on an ice-bath and separated crystals were filtered off, washed with ethanol and isopropyl ether, and dried to give 50.78 g of 5-carbamoyl-1-(4-nitrobenzyl)imidazolium-4-olate.

Workup

  1. temperatureunder refluxing
  2. customAnd then separated crystals
  3. filtrationwere filtered off
  4. washwashed with ethanol and isopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-98464c4a2da844be94b5099d8adaa04f
Source dataset
uspto-grants-1984_08
Patent number
US04464531

Reaction notes

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