Thionyl Chloride → HCID 22099893, compound

HRID 1290926Notes

Reaction equation

HRID 1290926 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:11][C:12]1[N:17]=[CH:16][C:15]([C:18]([OH:20])=O)=[CH:14][CH:13]=1)=[O:10].S(Cl)([Cl:23])=O>>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:11][C:12]1[N:17]=[CH:16][C:15]([C:18]([Cl:23])=[O:20])=[CH:14][CH:13]=1)=[O:10]

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 22099647HCID 22099647, compound

Product 1

HCID 22099893HCID 22099893, compound

Procedure

A mixture of 4.5 g of 6-[(2-methylbenzeneacetyl)amino]pyridine-3-carboxylic acid and 17 ml of thionyl chloride is heated on a steam bath for 1/2 hour. An additional 815 ml of thionyl chloride is added and the mixture refluxed for 0.5 hour. The volatiles are removed under vacuum and toluene (20 ml) added (twice) and the solvent removed under vacuum to give 5.3 g of a dark colored solid.

Workup

  1. temperatureis heated on a steam bath for 1/2 hour
  2. temperaturethe mixture refluxed for 0.5 hour
  3. customThe volatiles are removed under vacuum and toluene (20 ml)
  4. additionadded (twice) and the solvent
  5. customremoved under vacuum

Sources & evidence

ORD record
ord-2b6f098f1e8f43bf8f52b1df70d8f6ac
Source dataset
uspto-grants-1998_05
Patent number
US05753648

Reaction notes

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