Thionyl Chloride → HCID 20375639, compound

HRID 1390298Notes

Reaction equation

HRID 1390298 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][C:6]1[CH:29]=[CH:28][C:9]([CH2:10][N:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[C:14]([CH:22]([CH3:26])[C:23](O)=[O:24])=[CH:13][C:12]2=[O:27])=[CH:8][CH:7]=1>C1(C)C=CC=CC=1>[CH3:5][C:6]1[CH:29]=[CH:28][C:9]([CH2:10][N:11]2[C:20]3[C:15](=[CH:16][C:17]([CH3:21])=[CH:18][CH:19]=3)[C:14]([CH:22]([CH3:26])[C:23]([Cl:3])=[O:24])=[CH:13][C:12]2=[O:27])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12802696HCID 12802696, compound

Product 1

HCID 20375639HCID 20375639, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (0.109 ml.) was added by syringe to a suspension of α-[1-(4-methylbenzyl)-6-methyl-1,2-dihydro-2-oxoquinol-4-yl]propionic acid (0.335 g.) in toluene (3.5 ml.) (dried over sodium wire). The mixture was heated under reflux until evolution of gas ceased, and was then evaporated in vacuo. The residue was mixed with further dry toluene (5 ml.) and then evaporated in vacuo, and dried at ambient temperature under high vacuum, to give α-[1(4-methylbenzyl)-6-methyl-1,2-dihydro-2-oxoquinol-4-yl]propionyl chloride, which was dissolved without purification in dry toluene (2.5 ml.). The solution thus obtained was added by syringe to a solution of phenol (0.052 g.) in pyridine (0.044 ml.). The mixture was then stirred at ambient temperature for 45 minutes and then at 80° C. for 30 minutes. After being left at ambient temperature overnight, the reaction solution was mixed with ethyl acetate (20 ml.). The solution was then washed successively with 2N-hydrochloric acid (20 ml.), water (20 ml.), 2N-sodium hydroxide solution (2 × 20 ml.), water (20 ml.) and then saturated sodium chloride solution (20 ml.). The organic phase was separated, dried (MgSO4) and evaporated in vacuo. The residue was recrystallised from cyclohexane to give phenyl α-[1-(4-methylbenzyl)-6-methyl-1,2-dihydro-2-oxoquinol-4-yl]propionate, m.p. 111°-113° C., in 58% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux until evolution of gas
  3. customwas then evaporated in vacuo
  4. additionThe residue was mixed with further dry toluene (5 ml.)
  5. customevaporated in vacuo
  6. customdried at ambient temperature under high vacuum

Sources & evidence

ORD record
ord-98829e44188d4735b76272711b27e803
Source dataset
uspto-grants-1979_02
Patent number
US04138490

Reaction notes

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