Thionyl Chloride → 5-(Chloromethyl)-1,2-oxazole-3-carbonyl chloride

HRID 1952847Notes

Reaction equation

HRID 1952847 reaction equation
[Cl:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([OH:10])=O)[CH:4]=1.S(Cl)([Cl:13])=O>N1C=CC=CC=1>[Cl:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([Cl:13])=[O:10])[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 218664495-(Chloromethyl)-1,2-oxazole-3-carboxylic acid

Product 1

HCID 130018995-(Chloromethyl)-1,2-oxazole-3-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

120 g (743 mmol) of 5-chloromethylisoxazole-3-carboxylic acid were refluxed together with 500 ml of thionyl chloride and 2 drops of pyridine for 10 h, then concentrated under reduced pressure and subsequently distilled under 20 torr. The product distilled at 125-133° C. to result in 78 g (58% of theory).

Workup

  1. concentrationconcentrated under reduced pressure
  2. distillationsubsequently distilled under 20 torr
  3. distillationThe product distilled at 125-133° C.
  4. customto result in 78 g (58% of theory)

Sources & evidence

ORD record
ord-4eec5157effa424dbf14b7ea8105e34c
Source dataset
uspto-grants-2000_09
Patent number
US06114358

Reaction notes

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