Thionyl Chloride → HCID 20505953, compound

HRID 1703705Notes

Reaction equation

HRID 1703705 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-46ecb2b0891547eb93c9324815f1ea64
Source dataset
uspto-grants-1978_11
Patent number
US04124590

Reaction notes

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