Thionyl Chloride → HCID 178521122, compound

HRID 2419807Notes

Reaction equation

HRID 2419807 reaction equation
S(Cl)([Cl:3])=O.[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[C:16]([OH:18])=O>C1C=CC=CC=1>[OH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[CH:8][C:7]=1[C:16]([Cl:3])=[O:18]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178524710HCID 178524710, compound

Product 1

HCID 178521122HCID 178521122, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3.8 ml of thionyl chloride were added to a suspension of 8.2 g of 4-hydroxy-quinoline-3-carboxylic acid in 160 ml of benzene and the mixture was refluxed for an hour and then cooled. The mixture was vacuum filtered and the precipiate was empasted with a little anhydrous benzene and was dried to obtain 9 g of 4-hydroxy-quinoline-3-carboxylic acid chloride melting at 260° C. The said product was then reacted with 4.35 g of 2-aminothiazole as in Example 1 to obtain 4.3 g of N-(2-thiazolyl)-4-hydroxy-quinoline-3-carboxamide melting at 349°-350° C.

Workup

  1. temperaturethe mixture was refluxed for an hour
  2. temperaturecooled
  3. filtrationfiltered
  4. customwas dried

Sources & evidence

ORD record
ord-09c62304b70d4e57afab9a53090f78e4
Source dataset
uspto-grants-1978_08
Patent number
US04107310

Reaction notes

Loading…