N-methyl-2-pyrrolidone → HCID 178448078, compound

HRID 1707530Notes

Reaction equation

HRID 1707530 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([CH:9]2[O:14][CH2:13][CH:12]([CH:15]3[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][CH3:23])[CH2:17][CH2:16]3)[CH2:11][O:10]2)=[CH:4][C:3]=1[F:24].[CH3:25][N:26]1C(=O)CCC1>>[C:25]([C:2]1[C:7]([F:8])=[CH:6][C:5]([C@H:9]2[O:14][CH2:13][C@H:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([CH2:21][CH2:22][CH3:23])[CH2:17][CH2:16]3)[CH2:11][O:10]2)=[CH:4][C:3]=1[F:24])#[N:26]

Participants

3

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 189615332-(4'-Bromo-3',5'-difluorophenyl)-5-(4'-propylcyclohexyl)-1,3-dioxane

Product 1

HCID 178448078HCID 178448078, compound

Procedure

7.3 g (0.018 mol) of 2-(4'-bromo-3',5'-difluorophenyl)-5-(4'-propylcyclohexyl)-1,3-dioxane, 2.5 g (0.027 mol) of CuCN2 and 54 cm3 of NMP were refluxed for 2 hours with a mantle heater. After cooling the reactant to room temperature, 40 cm3 of EDA was added, it was poured into 50 cm3 of ice water, extracted with chloroform and washed with an aqueous EDA solution and water. The chloroform was removed, and the residue was dissolved in hexane and washed with water to remove the NMP. The hexane was removed, and the residue was treated in a silica gel column with chloroform as the solvent. The chloroform was removed, and the residue was repeatedly recrystallized in a solvent mixture of acetone and methanol until there were no cis forms to obtain 1.4 g (0.004 mol) of trans-2-(4'-cyano-3',5'-difluorophenyl)-5-(trans-4'-propylcyclohexyl)-1,3-dioxane. The phase transition temperature of this compound was measured with DSC as follows. ##STR17## (here, C shows crystals, N shows the nematic phase and I shows isotropic liquid.)

Workup

  1. addition40 cm3 of EDA was added
  2. extractionextracted with chloroform
  3. washwashed with an aqueous EDA solution and water
  4. customThe chloroform was removed
  5. dissolutionthe residue was dissolved in hexane
  6. washwashed with water
  7. customto remove the NMP
  8. customThe hexane was removed
  9. additionthe residue was treated in a silica gel column with chloroform as the solvent
  10. customThe chloroform was removed
  11. customthe residue was repeatedly recrystallized in a solvent mixture of acetone and methanol until there

Sources & evidence

ORD record
ord-40893ff6e4ea4a2b95a175bd828872bc
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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