Ethyl orthoformate → HCID 178513772, compound

HRID 358144Notes

Reaction equation

HRID 358144 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH:9][CH:10]([C:14]([NH2:16])=[O:15])[C:11]([NH2:13])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH:19](OCC)(OCC)OCC>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:14]([C:10]1[N+:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:18][CH:17]=2)=[CH:19][NH:13][C:11]=1[O-:12])(=[O:15])[NH2:16]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 132716292-{[(4-Nitrophenyl)methyl]amino}propanediamide

Product 1

HCID 178513772HCID 178513772, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 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 in an argon atmosphere
  2. temperatureThe reaction mixture was cooled on an ice-bath
  3. customseparated crystals
  4. filtrationwere filtered off
  5. washwashed with ethanol and isopropyl ether
  6. customdried

Sources & evidence

ORD record
ord-ac0ea3bab2264e58bd660b6fc49b6e9f
Source dataset
uspto-grants-1984_08
Patent number
US04464531

Reaction notes

Loading…