Thionyl Chloride → HCID 22099893, compound

HRID 976386Notes

Reaction equation

HRID 976386 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-2be79d6744484105a3ae175b1430426f
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Reaction notes

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