Thionyl Chloride → 2-{4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionyl chloride

HRID 1446886Notes

Reaction equation

HRID 1446886 reaction equation
[CH3:1][N:2]([C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19](O)=[O:20])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1.S(Cl)([Cl:27])=O>C(Cl)(Cl)Cl>[CH3:1][N:2]([C:13]1[CH:24]=[CH:23][C:16]([O:17][CH:18]([CH3:22])[C:19]([Cl:27])=[O:20])=[CH:15][CH:14]=1)[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 133148242-{4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionic acid

Product 1

HCID 205535162-{4-[N-Methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2-{4-[N-methyl-N-(5-chloro-2-benzoxazolyl)amino]phenoxy}propionic acid (3.0 g, 0.0087 mole; see Example 9), thionyl chloride (0.76 ml, 0.01 mole) and chloroform (25 ml) was heated under reflux for a period of 3 hours. The reaction mixture was cooled and the solvent and excess thionyl chloride was removed by distillation under reduced pressure to give the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 3 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent and excess thionyl chloride was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-e6c132bf0d2f4d348c05bbfeaeaf403f
Source dataset
uspto-grants-1982_02
Patent number
US04314065

Reaction notes

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