Thionyl Chloride → HCID 20505953, compound

HRID 355130Notes

Reaction equation

HRID 355130 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 20505953HCID 20505953, compound

Procedure

2-Chloro-5-(4-hydroxymethylpiperidinosulfonyl)benzoic acid (5.0 g.) is refluxed overnight with 50 ml. of thionyl chloride. After 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. customAfter 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-9e448a844b7e4a19a555800dcc651063
Source dataset
uspto-grants-1983_03
Patent number
US04377521

Reaction notes

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