Hydrochloric Acid → HCID 19040918, compound

HRID 866063Notes

Reaction equation

HRID 866063 reaction equation
[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=2)([OH:17])[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.[ClH:31]>C(OCC)C>[ClH:31].[F:29][C:2]([F:1])([F:30])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:26])[F:27])=[CH:20][CH:19]=2)([OH:17])[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 19040916HCID 19040916, compound

Product 1

HCID 19040918HCID 19040918, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 17.6 grams (0.041 mole) of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]pyridine in 200 mL of diethyl ether was added about 20 mL of an ethanolic solution saturated with hydrogen chloride. Upon completion of addition, the reaction mixture was cooled to promote precipitation of the product. When the solid precipitate did not appear, the reaction mixture was slowly concentrated during a one hour period by passing a stream of nitrogen gas over the reaction mixture. During this time the solid precipitate still did not appear. Additional diethyl ether was added, and the stream of nitrogen gas over the reaction mixture was continued. The reaction mixture was finally concentrated under reduced pressure to near dryness, at which point a solid precipitate formed. The solid was slurried in about 10 mL of fresh diethyl ether and filtered to yield 9.3 grams of 4-[bis(4-trifluoromethoxyphenyl)hydroxymethyl]pyridine hydrochloride. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperaturethe reaction mixture was cooled
  3. customprecipitation of the product
  4. concentrationthe reaction mixture was slowly concentrated during a one hour period
  5. additionAdditional diethyl ether was added
  6. concentrationThe reaction mixture was finally concentrated under reduced pressure
  7. customat which point a solid precipitate formed
  8. filtrationfiltered

Sources & evidence

ORD record
ord-9151415315664cd4b9c9e288af244ae9
Source dataset
uspto-grants-1996_10
Patent number
US05569664

Reaction notes

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