Heptanoic Acid → HCID 20095045, compound

HRID 1770159Notes

Reaction equation

HRID 1770159 reaction equation
[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[N:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=4)=[CH:20][N:19]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:31](O)(=[O:38])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].C1CCC(N=C=NC2CCCCC2)CC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]3[N:23]=[CH:22][C:21]([C:24]4[CH:29]=[CH:28][C:27]([O:30][C:31](=[O:38])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:26][CH:25]=4)=[CH:20][N:19]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 8094Heptanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 20095042HCID 20095042, compound

Product 1

HCID 20095045HCID 20095045, compoundYield 72.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.15 g (0.37 mM) of 2-octyl-5-[5-(4-hydroxyphenyl)pyrimidine-2-yl]indan, 0.05 g (0.38 mM) of heptanoic acid, 0.08 g (0.39 mM) of DCC, 0.01 g of 4-dimethylaminopyridine and 3 ml of methylene chloride were mixed and stirred for 5 hours at room temperature. The resultant N,N'-dichlorhexylurea 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/ethyl acetate=100/1) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.14 g of 2-octyl-5-[5-(4-heptanoyloxyphenyl)pyrimidine-2-yl]indan (Yield: 72.9%). ##STR143##

Workup

  1. filtrationThe resultant N,N'-dichlorhexylurea 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/ethyl acetate=100/1)
  6. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-cffe2dc2bebe40d8bce791c0dbd8526b
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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