Pyridine → HCID 20476830, compound

HRID 905042Notes

Reaction equation

HRID 905042 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:21])[C:10](=[N:13][C:14]3[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=3)[S:11][CH:12]=2)=[CH:4][C:3]=1[S:22](=[O:27])(=[O:26])[N:23]([CH3:25])[CH3:24].[C:28](Cl)(=[O:31])[CH2:29][CH3:30].N1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:21])[C:10](=[N:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][C:28](=[O:31])[CH2:29][CH3:30])=[CH:18][CH:19]=3)[S:11][CH:12]=2)=[CH:4][C:3]=1[S:22](=[O:27])(=[O:26])[N:23]([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 13091806HCID 13091806, compound

Product 1

HCID 20476830HCID 20476830, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2 g (4.7 mmoles) of 4-(4-chloro-3-dimethylsulfamoylphenyl)-2-(4-hydroxyphenylimino)-3-methyl-4-thiazoline is suspended in 40 ml of dry chloroform. 0.4 g (4.7 mmoles) of propionyl chloride (dissolved in 10 ml of chloroform) and 1.4 g (18 mmoles) of pyridine are added in that order. A slightly exothermic reaction produces, temporarily, a solution from which a yellow solid precipitates. After stirring for 3 hours at room temperature, a further 0.4 ml of propionyl chloride is added. The resulting yellow solution is allowed to stand for 3 days at room temperature and then evaporated to dryness in vacuo, the residue is distributed between water and ethyl acetate, the organic phase is dried and evaporated and the residue is recrystallized from isopropanol. Colorless crystals of m.p. 155°-159° C.

Workup

  1. customA slightly exothermic reaction
  2. customproduces
  3. customtemporarily, a solution from which a yellow solid precipitates
  4. additiona further 0.4 ml of propionyl chloride is added
  5. waitto stand for 3 days at room temperature
  6. customevaporated to dryness in vacuo
  7. customthe organic phase is dried
  8. customevaporated
  9. customthe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-687f91164be94e0a8cb9c4c6fc31ac94
Source dataset
uspto-grants-1983_12
Patent number
US04421757

Reaction notes

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