Pyridine → HCID 178443473, compound

HRID 1650604Notes

Reaction equation

HRID 1650604 reaction equation
[CH2:1]([C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](Cl)=[O:16])[CH2:11][CH2:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(Cl)(=O)C(Cl)=O.[F:24][C:25]1[C:30]([F:31])=[C:29]([C:32]#[N:33])[CH:28]=[CH:27][C:26]=1[OH:34].N1C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[CH2:1]([C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]([O:34][C:26]2[CH:27]=[CH:28][C:29]([C:32]#[N:33])=[C:30]([F:31])[C:25]=2[F:24])=[O:16])[CH2:13][CH2:14]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 27369782,3-Difluoro-4-hydroxybenzonitrileHCID 178443472HCID 178443472, compound

Product 1

HCID 178443473HCID 178443473, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.1 mole of trans-4-octylcyclohexanecarbonyl chloride (prepared from the carboxylic acid with oxalyl chloride in toluene) and 75 ml of methylene dichloride is added to a mixture of 0.1 mole of 2,3-difluoro-4-cyanophenol (prepared as in Example 1), 0.12 mole of pyridine, 10 mmole of 4-N,N-dimethylaminopyridine and 250 ml of methylene dichloride. After being stirred for 10 hours at room temperature, the mixture is washed with dilute hydrochloric acid, saturated sodium bicarbonate solution and water. Working up in the customary manner gives 4-(trans-4-octylcyclohexanecarbonyloxy)-2,3-difluorobenzonitrile.

Workup

  1. washthe mixture is washed with dilute hydrochloric acid, saturated sodium bicarbonate solution and water

Sources & evidence

ORD record
ord-f29e778f9cef43aaa3ea3410263e8cea
Source dataset
uspto-grants-1990_05
Patent number
US04925590

Reaction notes

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