Dicyclohexylcarbodiimide → HCID 19979937, compound

HRID 477296Notes

Reaction equation

HRID 477296 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32][CH:31]=2)=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:39]([C:41]1([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:46][CH2:45][CH:44](O)[CH2:43][CH2:42]1)#[N:40].C([C@H]1CC[C@H](O)CC1)#N.C(I)CCCCCC.C([N-]C(C)C)(C)C.[Li+]>ClCCl.CCOCC>[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[CH:31]=[CH:32][C:33]([C:36]([O:38][CH:44]3[CH2:45][CH2:46][C:41]([C:39]#[N:40])([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH3:54])[CH2:42][CH2:43]3)=[O:37])=[CH:34][CH:35]=2)=[CH:26][CH:25]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

9

Reactant 6

HCID 10868DicyclohexylcarbodiimideHCID 202741-IodoheptaneHCID 2724682Lithium diisopropylamideHCID 44339084'-(Heptyloxy)[1,1'-biphenyl]-4-carboxylic acidHCID 19979915HCID 19979915, compoundHCID 178511285HCID 178511285, compound

Product 1

HCID 19979937HCID 19979937, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

While cooling with ice, 4.54 g of dicyclohexylcarbodiimide in 10 ml of dichloromethane are added dropwise to a mixture of 6.24 g of 4-heptyloxy-4'-biphenylcarboxylic acid, 4.46 g of 4-cyano-4-heptylcyclohexanol [obtainable from trans-4-cyanocyclohexanol by protecting the hydroxyl group as THP ether, reaction with heptyl iodide and lithium diisopropylamide and subsequent cleavage of the protective group] and 0.2 g of 4-N,N'-dimethylaminopyridine in 45 ml of dichloromethane. After 25 hours, the precipitated urea derivative is filtered off by suction, the filtrate is diluted with methylene chloride and washing was carried out several times in sequence with dilute hydrochloric acid and with water. After drying, the removal of the solvent and purification by chromatography and crystallization, 4-cyano-4-heptylcyclohexyl 4-heptyloxy-4'-biphenylcarboxylate is obtained.

Workup

  1. filtrationthe precipitated urea derivative is filtered off by suction
  2. additionthe filtrate is diluted with methylene chloride
  3. washwashing
  4. customAfter drying
  5. customthe removal of the solvent and purification
  6. customby chromatography and crystallization

Sources & evidence

ORD record
ord-476f865ede454ea795b872dd43e935ed
Source dataset
uspto-grants-1989_12
Patent number
US04886620

Reaction notes

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