Cyclohexylamine → n-Cyclohexyl-5-(4-nitrophenyl)-1,3-thiazol-2-amine

HRID 23356Notes

Reaction equation

HRID 23356 reaction equation
Br[CH:2]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)[CH:3]=O.[S-:14][C:15]#[N:16].[K+].[CH:18]1([NH2:24])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>CO>[CH:18]1([NH:24][C:15]2[S:14][C:2]([C:5]3[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=3)=[CH:3][N:16]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 516872Potassium thiocyanateHCID 201888492-Bromo-2-(4-nitrophenyl)acetaldehyde

Product 1

HCID 12066444n-Cyclohexyl-5-(4-nitrophenyl)-1,3-thiazol-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of bromo(4-nitrophenyl)acetaldehyde and potassium thiocyanate (1.2 equivalents) in methanol is stirred at room temperature for 1 hour. The cyclohexylamine (1,05 equivalents) is added drop-wise and the mixture is heated under reflux until completion of the reaction (5-12 hours). After cooling to 0° C. the precipitate is filtered off and washed with water. The crude material is purified by usual silica gel chromatography to give the desired compound.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux until completion of the reaction (5-12 hours)
  3. filtrationis filtered off
  4. washwashed with water
  5. customThe crude material is purified by usual silica gel chromatography

Sources & evidence

ORD record
ord-14089d6065474121a1b9c499e0722165
Source dataset
uspto-grants-2005_02
Patent number
US06852720B2

Reaction notes

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