Dicyclohexylcarbodiimide → 4-(5-Undecyl-2-pyrimidinyl)-2-fluorophenyl 5-hexylthiophene-2-carboxylate

HRID 1608451Notes

Reaction equation

HRID 1608451 reaction equation
[CH2:1]([C:7]1[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:15]([C:26]1[CH:27]=[N:28][C:29]([C:32]2[CH:37]=[CH:36][C:35](O)=[C:34]([F:39])[CH:33]=2)=[N:30][CH:31]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.N1(C2C=CC=CN=2)CCCC1>[CH2:1]([C:7]1[S:11][C:10]([C:12]([O:14][C:35]2[CH:36]=[CH:37][C:32]([C:29]3[N:30]=[CH:31][C:26]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:27][N:28]=3)=[CH:33][C:34]=2[F:39])=[O:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 131282695-Hexyl-2-thiophenecarboxylic acidHCID 1356894144-(5-Undecyl-2-pyrimidinyl)-2-fluorophenol

Product 1

HCID 536789154-(5-Undecyl-2-pyrimidinyl)-2-fluorophenyl 5-hexylthiophene-2-carboxylateYield 73.1%

Reagents, catalysts & solvents 2

HCID 110190202-(Pyrrolidin-1-yl)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.0 g (4.72×10-3 mol) of 5-hexylthiophene-2-carboxylic acid, 1.62 g (4.72×10-3 mol) 4-(5-undecyl-2-pyrimidinyl)-2-fluorophenol, N,N'-dicyclohexylcarbodiimide (DCC) and 0.03 g of pyrrolidinopyridine were dissolved in 30 ml of dichloromethane, followed by stirring overnight at room temperature. After the reaction, the insoluble matter was filtered off, followed by distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: toluene) and recrystallized from a mixture solvent (ethanol/ethyl acetate) to obtain 1.86 g of a pure product (Yield: 3.2%) ##STR84##

Workup

  1. customAfter the reaction
  2. filtrationthe insoluble matter was filtered off
  3. customto obtain a crude product
  4. customThe crude product was purified by silica gel column chromatography (eluent: toluene)
  5. customrecrystallized from a mixture solvent (ethanol/ethyl acetate)

Sources & evidence

ORD record
ord-faca008d790c4b858083331f6bbd2bdf
Source dataset
uspto-grants-1995_03
Patent number
US05395551

Reaction notes

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