2,2,2-Trifluoroethanol → HCID 67938850, compound

HRID 622705Notes

Reaction equation

HRID 622705 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].[Na].Br[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[CH2:22][CH2:21][NH:20][C:19]2=[CH:23][N+:24]([O-:26])=[O:25])=[CH:13][N:12]=1>C1(C)C=CC=CC=1>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][N:18]2[CH2:22][CH2:21][NH:20][C:19]2=[CH:23][N+:24]([O-:26])=[O:25])=[CH:13][N:12]=1

Participants

6

Reactant 4

HCID 64092,2,2-Trifluoroethanol2×HCID 24758Sodium hydrideHCID 5360545SodiumHCID 85528837HCID 85528837, compound

Product 1

HCID 67938850HCID 67938850, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

2,2,2-Trifluoroethanol (3.6 g) was dissolved in toluene (20 ml), and sodium hydride (0.7 g) was added to prepare a sodium salt of 2,2,2-trifluoroethanol. Then, 3 g of 1-(2-bromo-5-pyridylmethyl)-2-(nitromethylene)imidazolidine (the known compound described in Japanese Patent Application No. 132,943/1984) was added, and the mixture was heated at 80° C. for 8 hours. Toluene was distilled off under reduced pressure, and the residue was poured into 20 ml of ice water and then neutralized. The aqueous solution was extracted with dichloromethane, and the extract was purified by silica gel column chromatography to give 1-[2-(2,2,2-trifluoroethoxy)-5-pyridylmethyl]-2-(nitromethylene)-imidazolidine. mp. 132°-135° C.

Workup

  1. addition132,943/1984) was added
  2. distillationToluene was distilled off under reduced pressure
  3. additionthe residue was poured into 20 ml of ice water
  4. extractionThe aqueous solution was extracted with dichloromethane
  5. customthe extract was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f16100821cc943d5b3100d9fffe02296
Source dataset
uspto-grants-1988_09
Patent number
US04772620

Reaction notes

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