Thionyl Chloride → 2-Chloro-5-(4-chloromethylpiperidinosulfonyl)benzoic Acid

HRID 1730595Notes

Reaction equation

HRID 1730595 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20]O)[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(Cl)([Cl:24])=O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[CH2:19][CH2:18][CH:17]([CH2:20][Cl:24])[CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 205058672-Chloro-5-(4-hydroxymethylpiperidinosulfonyl)benzoic acid

Product 1

HCID 205059532-Chloro-5-(4-chloromethylpiperidinosulfonyl)benzoic Acid

Procedure

2-Chloro-5-(4-hydroxymethylpiperidinosulfonyl)benzoic acid (5.0 g.) is refluxed oernight with 50 ml. of thionyl chloride. Afer evaporation to dryness, the residue is dissolved in 70 ml. of acetone, 30 ml. of water added and the mixture is allowed to stand at room temperature for a half hour. The solution is then filtered and concentrated to half volume. On the addition of 20 ml. of water a precipitated oil is obtained which crystallizes on stirring. Recrystallization from acetone-benzene yields the product, m.p. 175°-177° C.

Workup

  1. customAfer evaporation to dryness
  2. dissolutionthe residue is dissolved in 70 ml
  3. additionof water added
  4. waitto stand at room temperature for a half hour
  5. filtrationThe solution is then filtered
  6. concentrationconcentrated to half volume
  7. additionOn the addition of 20 ml
  8. customof water a precipitated oil is obtained which
  9. customcrystallizes
  10. customRecrystallization from acetone-benzene
  11. customyields the product, m.p. 175°-177° C.

Sources & evidence

ORD record
ord-f63afcf230214a929cde07a72cc0e74a
Source dataset
uspto-grants-1976_11
Patent number
US03992441

Reaction notes

Loading…