O-Phenylenediamine → 2-Cyclohexyl-1H-imidazole

HRID 1622057Notes

Reaction equation

HRID 1622057 reaction equation
[C:1]1([NH2:8])C=CC=C[C:2]=1[NH2:7].[CH:9]1([C:15](O)=O)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.[OH-].[Na+]>>[CH:9]1([C:15]2[NH:7][CH:2]=[CH:1][N:8]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 3

HCID 7243O-PhenylenediamineHCID 7413Cyclohexanecarboxylic acidHCID 14798Sodium Hydroxide

Product 1

HCID 111594052-Cyclohexyl-1H-imidazoleYield 91.5%

Conditions

Temperature
140 °C

Procedure

A mixture of 7 g of o-phenylenediamine and 12.5 g of cyclohexanecarboxylic acid was melted by heating at 130-150° C. and stirred for 8 hours. The solid after reaction was transferred into 130 g of 1 wt % sodium hydroxide aqueous solution to form a suspension, which was filtered and washed with hot water. The crude crystals thus obtained were recrystallized from methanol/water, filtered, and dried, obtaining 8.9 g of 2-cyclohexylimidazole (yield 69%).

Workup

  1. customThe solid after reaction
  2. customto form a suspension, which
  3. filtrationwas filtered
  4. washwashed with hot water
  5. customThe crude crystals thus obtained
  6. customwere recrystallized from methanol/water
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-278da7f643e0416cbf0fac0b49a8241c
Source dataset
uspto-grants-2014_07
Patent number
US08778591B2

Reaction notes

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