4-Fluorobenzoic Acid → HCID 20095060, compound

HRID 1770169Notes

Reaction equation

HRID 1770169 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]([OH:24])=[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].[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([OH:32])=O)=[CH:28][CH:27]=1.[CH2:35]1CCC(N=C=NC2CCCCC2)C[CH2:36]1>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]([O:24][C:30](=[O:32])[C:29]4[CH:28]=[CH:27][C:26]([F:25])=[CH:34][CH:33]=4)=[CH:20][N:19]=3)[CH:15]=2)[CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:35][CH3:36]

Participants

6

Reactant 3

HCID 99734-Fluorobenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 20095062HCID 20095062, compound

Product 1

HCID 20095060HCID 20095060, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

0.70 g (3.0 mM) of 2-octyl-5-(5-hydroxypyrimidine-2-yl)indan, 0.42 g (3.0 mM) of 4-fluorobenzoic acid, 0.62 g (3.0 mM) of DCC, 0.02 g of 4-dimethylaminopyridine and 20 ml of methylene chloride were mixed and stirred for 7 hours at room temperature to precipitate N,N'-dicyclohexaurea. The N,N'-dicyclohexylurea was recovered by filtration and washed with dichloromethane to be added to the filtrate. The resultant dichloromethane solution was evaporated into a residue under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (toluene/methanol) to obtain 0.70 g of 2-decyl-5-[5-(4-fluorobenzoyloxy)pyrimidine-2-yl]indan (Yield: 66.0%). ##STR299##

Workup

  1. customto precipitate N,N'-dicyclohexaurea
  2. filtrationThe N,N'-dicyclohexylurea was recovered by filtration
  3. washwashed with dichloromethane
  4. additionto be added to the filtrate
  5. customThe resultant dichloromethane solution was evaporated into a residue under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: toluene)
  7. customrecrystallized from a mixture solvent (toluene/methanol)

Sources & evidence

ORD record
ord-41e83cde7d4341b194d5de1182fcc950
Source dataset
uspto-grants-1995_01
Patent number
US05385692

Reaction notes

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