Thionyl Chloride → HCID 20519111, compound

HRID 2198506Notes

Reaction equation

HRID 2198506 reaction equation
[CH3:1][N:2]([C:14]1[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20](O)=[O:21])=[CH:16][CH:15]=1)[C:3]1[CH:12]=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:13])[CH:9]=2)[N:4]=1.S(Cl)([Cl:28])=O>>[CH3:1][N:2]([C:14]1[CH:25]=[CH:24][C:17]([O:18][CH:19]([CH3:23])[C:20]([Cl:28])=[O:21])=[CH:16][CH:15]=1)[C:3]1[CH:12]=[N:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:13])[CH:9]=2)[N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13323150HCID 13323150, compound

Product 1

HCID 20519111HCID 20519111, compound

Procedure

A mixture of 2-{4-[N-methyl-N-(6-chloroquinoxalin-2-yl)amino]phenoxy}propionic acid (2.0 g; compound no 27, Example 9) and thionyl chloride (25 ml) was heated under reflux for a period of 2 hours. The excess thionyl chloride was removed by distillation under reduced pressure to give 2-{4-[N-methyl-N-(6-chloroquinoxalin-2-yl)amino]phenoxy}propionyl chloride. A mixture of n-propanol (10 ml) and triethylamine (10 ml) was added and the mixture was stirred at room temperature for a period of 1 hour. The mixture was poured into water (200 ml) and the aqueous mixture was extracted with dichloromethane. The organic extract was washed several times with water and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the residue was chromatographed over alumina (eluent dichloromethane) to give n-propyl 2-{4-[N-methyl-N-(6-chloroquinoxalin-2-yl)amino]phenoxy}propionate as an oil.

Workup

  1. temperatureunder reflux for a period of 2 hours
  2. customThe excess thionyl chloride was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-04a629bb6bb34e46a54c3bb1c768e780
Source dataset
uspto-grants-1982_11
Patent number
US04358307

Reaction notes

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