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

HRID 1703706Notes

Reaction equation

HRID 1703706 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-f0cec35029a24644a61cd013f23c7a8a
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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