Methanol → HCID 10474496, compound

HRID 2058668Notes

Reaction equation

HRID 2058668 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].[CH:13]1([N:19]=[C:20]=[N:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C.C[OH:36]>>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([N:21]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:20]([NH:19][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)=[O:36])=[O:8])([O-:3])=[O:2]

Participants

5

Reactant 4

HCID 887Methanol2×HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 110872-Nitrobenzoic acid

Product 1

HCID 10474496HCID 10474496, compoundYield 45%

Procedure

A solution of 25 g (0.15 mol) of 2-nitro-benzoic acid in 75 ml of methanol was added dropwise to a boiling solution of 31 g (0.15 mol) of dicyclohexyl-carbodiimide and 8 ml of triethylamine in 300 ml of methanol. The reaction mixture was heated under reflux for 2 hours and stirred at room temperature overnight. After distilling off the solvent in vacuo, the residue was recrystallized from isopropanol. 25 g (45% of theory) of N-(2-nitrobenzoyl)-N,N'-dicyclohexyl-urea of melting point 134° C. were obtained.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 hours
  3. distillationAfter distilling off the solvent in vacuo
  4. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-e84b6f52ace74e1c85b2a5ae179a342e
Source dataset
uspto-grants-1982_03
Patent number
US04318924

Reaction notes

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