Potassio isocyanate → 4-nitro-2-methyl-N-(beta-ureido-ethyl)aniline

HRID 436334Notes

Reaction equation

HRID 436334 reaction equation
[N-:1]=[C:2]=[O:3].[K+].Cl.[N+:6]([C:9]1[CH:18]=[CH:17][C:12]([NH:13][CH2:14][CH2:15][NH2:16])=[C:11]([CH3:19])[CH:10]=1)([O-:8])=[O:7]>O>[N+:6]([C:9]1[CH:18]=[CH:17][C:12]([NH:13][CH2:14][CH2:15][NH:16][C:2]([NH2:1])=[O:3])=[C:11]([CH3:19])[CH:10]=1)([O-:8])=[O:7]

Participants

4

Reactant 2

HCID 11051572Potassio isocyanateHCID 17336835N-(2-methyl-4-nitrophenyl)ethane-1,2-diamine hydrochloride

Product 1

HCID 214541964-nitro-2-methyl-N-(beta-ureido-ethyl)anilineYield 80.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

24.3 g (0.3 mole) of potassium isocyanate in solution in 75 cm3 of water is added to 57.9g (0.25 mole) of 4-nitro-2-methyl-N-(β-aminoethyl) aniline monohydrochloride in 235 cm3 of water at 60°. After keeping the reaction mixture for 15 minutes in a boiling water bath, drying yields 48 g of 4-nitro-2-methyl-N-(β-ureido-ethyl)aniline which, after recrystallization in acetic acid, melts at 186° C.

Workup

  1. customfor 15 minutes
  2. customdrying

Sources & evidence

ORD record
ord-72984c75cfb44b0d8dba5c30d58b4764
Source dataset
uspto-grants-1977_02
Patent number
US04008272

Reaction notes

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