Benzyl Alcohol → HCID 21616424, compound

HRID 1032601Notes

Reaction equation

HRID 1032601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:11])[N:10]=1)[C:5](Cl)=[O:6].[CH2:12]([OH:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.N1C=CC=CC=1>C(#N)C.CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:12]([O:19][C:5](=[O:6])[C:4]1[CH:8]=[C:9]([Cl:11])[N:10]=[C:2]([Cl:1])[CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 27816432,6-Dichloro-isonicotinoyl chloride

Product 1

HCID 21616424HCID 21616424, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent2×HCID 6344DichloromethaneSolvent

Procedure

7.8 g of 2,6-dichloroisonicotinic acid chloride, dissolved in 10 ml of acetonitrile, are added dropwise to a solution, maintained at 15°-20° C. by cooling, of 5.4 g of benzyl alcohol, 0.5 g of 4-dimethylaminopyridine and 3.0 g of pyridine in 50 ml of acetonitrile. After stirring overnight at room temperature the batch is poured onto ice-water, taken up in methylene chloride, washed with water, dried and concentrated by evaporation. The oil that remains crystallises from pentane in the form of white crystals having a melting point of 39°-41° C.

Workup

  1. additionare added dropwise to a solution
  2. temperaturemaintained at 15°-20° C.
  3. additionis poured onto ice-water
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customThe oil that remains crystallises from pentane in the form of white crystals

Sources & evidence

ORD record
ord-2c65f57b2136470d9afdaf154eb181e2
Source dataset
uspto-grants-1990_09
Patent number
US04959096

Reaction notes

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