Water → HCID 20536216, compound

HRID 444094Notes

Reaction equation

HRID 444094 reaction equation
[S:1](Cl)(Cl)=[O:2].[C:5]([C:7]1[CH:8]=[CH:9][C:10]([OH:18])=[C:11]([C:13]([CH3:17])([CH3:16])[CH2:14][OH:15])[CH:12]=1)#[N:6].N1C=CC=CC=1.O>C(OCC)C>[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[O:18][S:1](=[O:2])[O:15][CH2:14][C:13]([CH3:16])([CH3:17])[C:11]=2[CH:12]=1)#[N:6]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 20536186HCID 20536186, compound

Product 1

HCID 20536216HCID 20536216, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Thionyl chloride (4.2 g) in diethyl ether (10 ml) was added dropwise with stirring at 0°-5° C. to a solution of 2-(5-cyano-2-hydroxyphenyl)-2-methyl-1-propanol (5 g) prepared as in Example 26, and pyridine (5.5 g) in diethyl ether (80 ml). The mixture was stirred for 3 hours at 0°-20° C. Water was then added and the mixture was filtered. The ether solution was then washed with dilute hydrochloric acid, when with aqueous sodium bicarbonate and water (twice), then dried over magnesium sulphate and run down. The residue was recrystallised from ethanol, giving the title product (2.0 g) as white crystals, mp 87°-88° C.

Workup

  1. filtrationthe mixture was filtered
  2. washThe ether solution was then washed with dilute hydrochloric acid, when with aqueous sodium bicarbonate and water (twice),
  3. dry with materialthen dried over magnesium sulphate
  4. customThe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-80ee9ec5c92f48ea826989e38ffb9ff0
Source dataset
uspto-grants-1981_04
Patent number
US04263037

Reaction notes

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