Hydrochloric Acid → 2-Chloro-5-(1,2,5,6-tetrahydropyridylsulfonyl)benzoic Acid

HRID 1390502Notes

Reaction equation

HRID 1390502 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[NH:15]1[CH2:20][CH2:19][CH:18]=[CH:17][CH2:16]1.Cl>O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:15]2[CH2:20][CH2:19][CH:18]=[CH:17][CH2:16]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 127501,2,3,6-TetrahydropyridineHCID 67306Benzoic acid, 2-chloro-5-(chlorosulfonyl)-

Product 1

HCID 571773882-Chloro-5-(1,2,5,6-tetrahydropyridylsulfonyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Chloro-5-chlorosulfonylbenzoic acid (25.5 g.) is added in small portions over a 5 minute period with cooling to a solution of 1,2,5,6-tetrahydropyridine (25.0 g.) in 200 ml. of water. After stirring at room temperature for a half hour, the reaction mixture is acidified with concentrated hydrochloric acid. The crystalline precipitate is filtered off and dissolved in 75 ml. of methylene chloride and 10 ml. of ether. After concentration to 50 ml., hexane is added to turbidity, affording crystals, m.p. 180°-182° C.

Workup

  1. filtrationThe crystalline precipitate is filtered off
  2. dissolutiondissolved in 75 ml
  3. concentrationAfter concentration to 50 ml
  4. addition, hexane is added to turbidity
  5. customaffording crystals, m.p. 180°-182° C.

Sources & evidence

ORD record
ord-e459da4aafc54f76aa3fffbfb310b6dc
Source dataset
uspto-grants-1979_02
Patent number
US04138399

Reaction notes

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