Hydrazinecarboxylic acid, ethyl ester → 1-Ethoxycarbonyl-4-methoxycarbonylmethyl-semicarbazide

HRID 1660119Notes

Reaction equation

HRID 1660119 reaction equation
[CH3:1][O:2][C:3]([CH2:5][N:6]=[C:7]=[O:8])=[O:4].[CH2:9]([O:11][C:12]([NH:14][NH2:15])=[O:13])[CH3:10]>C1(C)C=CC=CC=1>[CH2:9]([O:11][C:12]([NH:14][NH:15][C:7]([NH:6][CH2:5][C:3]([O:2][CH3:1])=[O:4])=[O:8])=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 2769479Methyl 2-isocyanatoacetate

Product 1

HCID 205575511-Ethoxycarbonyl-4-methoxycarbonylmethyl-semicarbazideYield 76.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 19.72 g (0.17 mol) of methoxycarbonylmethyl isocyanate in 70 ml of dry toluene was added dropwise at room temperature to a stirred solution of 18.00 g (0.17 mol) of ethoxycarbonylhydrazine in 400 ml of dry toluene. The mixture was stirred at room temperature overnight and filtered. The colourless solid was washed with toluene, dried and recrystallized from ethyl acetate to give 28.54 g (76%) of 1-ethoxycarbonyl-4-methoxycarbonylmethyl-semicarbazide of melting point 116°-121° C.

Workup

  1. filtrationfiltered
  2. washThe colourless solid was washed with toluene
  3. customdried
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-2cd99f0fc1cd4675a1be862352851a46
Source dataset
uspto-grants-1981_12
Patent number
US04307094

Reaction notes

Loading…