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Hydrochloric Acid → N-(Cyclohexylmethyl)-N'-(2,6-diethylphenyl)-N-(4-phenylcyclohexyl)carbamimidic acid

HRID 37296
Notes
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Reaction equation

HRID 37296 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][CH:10]([NH:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH2:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][CH3:36])[C:30]=1[N:37]=[C:38]=[O:39])[CH3:28].Cl>ClCCl>[CH2:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][CH3:36])[C:30]=1[NH:37][C:38]([N:13]([CH2:14][CH:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[CH:10]1[CH2:9][CH2:8][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:12][CH2:11]1)=[O:39])[CH3:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 51531832,6-Diethylphenyl isocyanateHCID 19935094N-(4-phenylcyclohexyl)-N-cyclohexylmethylamine

Product 1

HCID 3072997N-(Cyclohexylmethyl)-N'-(2,6-diethylphenyl)-N-(4-phenylcyclohexyl)carbamimidic acidYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To the solution of 2 g of N-(4-phenylcyclohexyl)-N-cyclohexylmethylamine in dichloromethane was added 2 ml of pyridine and to the mixture was added a solution of 1.6 g of 2,6-diethylphenylisocyanate in 30 ml of dichloromethane dropwise. After the mixture was stirred at room temperature, to the solution was added diluted hydrochloric acid and extracted with ethyl acetate. The extract was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine and then dried over magnesium sulfate. The solvent was distilled away in vacuo to give 2 g of crude crystals. The crystals were recrystallized from the mixture of ethyl acetate and hexane to give 1.2 g of N-(2,6-diethylphenyl)-N'-cyclohexylmethyl-N'-(4-phenylcyclohexyl)urea, melting at 166°-168° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled away in vacuo
  5. customto give 2 g of crude crystals
  6. customThe crystals were recrystallized from the mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-03085be664434eebbe7e6fc4b41d7bde
Source dataset
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05420164

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes