Dicyclohexylcarbodiimide → HCID 178444281, compound

HRID 1906331Notes

Reaction equation

HRID 1906331 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([OH:15])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[CH2:16]([C@H:21]1[CH2:26][CH2:25][C@H:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([C:39](O)=[O:40])=[CH:35][CH:34]=3)=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)[CH2:17][CH2:18][CH2:19][CH3:20].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C@H:9]2[CH2:14][CH2:13][C@H:12]([O:15][C:39]([C:36]3[CH:35]=[CH:34][C:33]([C:30]4[CH:31]=[CH:32][C:27]([C@H:24]5[CH2:25][CH2:26][C@H:21]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:22][CH2:23]5)=[CH:28][CH:29]=4)=[CH:38][CH:37]=3)=[O:40])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 178444279HCID 178444279, compoundHCID 178509806HCID 178509806, compound

Product 1

HCID 178444281HCID 178444281, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g of trans-4-(p-cyanophenyl)cyclohexanol, 1.75 g of 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxylic acid, 1.2 g of dicyclohexylcarbodiimide and 98 mg of 4-(dimethylamino)pyridine in 60 ml of dichloromethane was stirred at room temperature for 18 hours under argon gasification. The beige suspension was subsequently filtered (rinsing with dichloromethane) and the filtrate was concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.1 g) on silica gel with toluene yielded 1.2 g (45%) of pure 4'-(trans-4-pentylcyclohexyl)-4-biphenylcarboxylic acid trans-4-(p-cyanophenyl)cyclohexyl ester. Recrystallization from ethyl acetate/acetone (vol. 1:4) gave white crystals of m.p. (C-N) 148.6° C. and cl.p. (N-I) 347° C.; purity 99.6%.

Workup

  1. filtrationThe beige suspension was subsequently filtered
  2. wash(rinsing with dichloromethane)
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0f1e23959c43402499926b2a57bc75ed
Source dataset
uspto-grants-1987_03
Patent number
US04652089

Reaction notes

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