Dicyclohexylcarbodiimide → HCID 20095050, compound

HRID 1770150Notes

Reaction equation

HRID 1770150 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([OH:20])=[O:19])[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:21]([C:31]1[CH:32]=[N:33][C:34]([C:37]2[CH:42]=[CH:41][C:40](O)=[CH:39][CH:38]=2)=[N:35][CH:36]=1)[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]([O:20][C:40]3[CH:39]=[CH:38][C:37]([C:34]4[N:33]=[CH:32][C:31]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:36][N:35]=4)=[CH:42][CH:41]=3)=[O:19])[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 20095034HCID 20095034, compoundHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 20095050HCID 20095050, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.00 g (3.64 mM) of 2-octylindan-5-carboxylic acid and 1.13 g (3.62 mM) of 5-decyl-2-(4-hydroxyphenyl)pyrimidine were dissolved in 30 ml of dichloromethane. To the solution, 0.74 g (3.59 mM) of N,N'-dicyclohexylcarbodiimide (DCC) and 0.05 g of 4-pyrrolidinopyridine were added, followed by stirring for 5 hours. The resultant N,N'-dicyclohexylurea was recovered by filtration, washed with dichloromethane, and added to the filtrate. The resultant dichloromethane solution was subjected to distillation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/methanol) to obtain 1.23 g of 4-(5-decylpyrimidine-2-yl)phenyl 2-octylindan-5-carboxylate (Yield: 60.3%). ##STR131##

Workup

  1. filtrationThe resultant N,N'-dicyclohexylurea was recovered by filtration
  2. washwashed with dichloromethane
  3. additionadded to the filtrate
  4. distillationThe resultant dichloromethane solution was subjected to distillation under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  6. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-677f0f8c92ab42f78879d5f3f1ee1970
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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