Chloride → HCID 20505900, compound

HRID 1730603Notes

Reaction equation

HRID 1730603 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[C:7]([Cl:15])[C:3]=1[C:4]([OH:6])=[O:5].[NH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[Cl-]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)(=[O:13])=[O:12])=[C:7]([Cl:15])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 312ChlorideHCID 8082PiperidineHCID 35382162,6-dichloro-3-chlorosulfonyl-benzoic Acid

Product 1

HCID 20505900HCID 20505900, compound

Procedure

2,6-Dichloro-5-chlorosulfonylbenzoic acid (960 mg.; 3.3 m moles) is added portion-wise to 1.95 g. (0.0165 mole) of piperidine in 15 ml. of drymethylene chloride, and the mixture heated to reflux for 1.5 hrs. The solvent and excess amine are removed under reduced pressure and the residue dissolved in 15 ml. of 2N sodium hydroxide. The aqueous base solution is extracted (2 x 50 ml.) with ether and acidified with 6N hydrochloric acid. The precipitated gum is filtered, dried and allowed to crystallize in hexane, 1.1 g., m.p. 145°-150° C. A small sample is recrystallized from acetonitrile, m.p. 142°-145° C.

Workup

  1. temperatureto reflux for 1.5 hrs
  2. customThe solvent and excess amine are removed under reduced pressure
  3. dissolutionthe residue dissolved in 15 ml
  4. extractionThe aqueous base solution is extracted (2 x 50 ml.) with ether
  5. filtrationThe precipitated gum is filtered
  6. customdried
  7. customto crystallize in hexane
  8. customA small sample is recrystallized from acetonitrile, m.p. 142°-145° C.

Sources & evidence

ORD record
ord-aaab80451448491684ac4331af6d0602
Source dataset
uspto-grants-1976_11
Patent number
US03992441

Reaction notes

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