N-Methylcyclohexylamine → 4-amino-2-chloro-N-cyclohexyl-N-methylbenzamide

HRID 838991Notes

Reaction equation

HRID 838991 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]2[CH:12]=[CH:11]N=[CH:9]2)=[O:7])=[C:4]([Cl:15])[CH:3]=1.CN[CH:18]1[CH2:23]CC[CH2:20][CH2:19]1>C(Cl)(Cl)Cl>[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([N:8]([CH:12]2[CH2:11][CH2:20][CH2:19][CH2:18][CH2:23]2)[CH3:9])=[O:7])=[C:4]([Cl:15])[CH:3]=1

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 20325582HCID 20325582, compound

Product 1

HCID 167931254-amino-2-chloro-N-cyclohexyl-N-methylbenzamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 15 gm of N-(4-amino-2-chloro-benzoyl)-imidazole (m.p. 122°-127° C) and 150 ml of N-methyl-cyclohexylamine was stirred at 130° C for 4 hours. Subsequently, chloroform was added to the reaction mixture, and the resulting mixture was extracted twice with 300 ml of water. The organic phase was dried with sodium sulfate and evaporated. The oily residue was purified by chromatography on a silicagel column with chloroform/methanol (6:1), and the combined eluate fractions containing the desired product were evaporated. The residue was crystallized from isopropanol, yielding 4-amino-2-chloro-N-cyclohexyl-N-methyl-benzoic acid amide, m.p. 166°-170° C.

Workup

  1. extractionthe resulting mixture was extracted twice with 300 ml of water
  2. dry with materialThe organic phase was dried with sodium sulfate
  3. customevaporated
  4. customThe oily residue was purified by chromatography on a silicagel column with chloroform/methanol (6:1)
  5. additionthe combined eluate fractions containing the desired product
  6. customwere evaporated
  7. customThe residue was crystallized from isopropanol

Sources & evidence

ORD record
ord-ed733cfc59ee4695a282ba54ea8c39d3
Source dataset
uspto-grants-1978_06
Patent number
US04093734

Reaction notes

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