Acetic Acid → HCID 86749793, compound

HRID 742186Notes

Reaction equation

HRID 742186 reaction equation
[Cl:1][C:2]1[S:6][N:5]([CH2:7][CH2:8][CH2:9][C:10](OC)=[O:11])[C:4](=[O:14])[CH:3]=1.Cl.C(O)(=[O:18])C>>[Cl:1][C:2]1[S:6][N:5]([CH2:7][CH2:8][C:9](=[C:10]=[O:11])[OH:18])[C:4](=[O:14])[CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 19425177HCID 19425177, compound

Product 1

HCID 86749793HCID 86749793, compound

Procedure

The methyl ester of the isothiazolones were hydrolyzed to the free acids. 5-Chloro-2-(3-methoxycarbonylpropyl)-3-isothiazolone (4.0 g) was taken up in 6 ml of acetic acid. To this stirred solution at room temperature was added 6M aqueous HCl (7 ml). This solution was then stirred at room temperature for 24 hours, during which time a white precipitate formed. The solution was filtered and the filtrate further concentrated to yield more of the same precipitate (5-chloro-2-(3-hydroxy-carbonylpropyl)-3-isothiazolone). The combined yield was 2.95 g (m.p. 158°-161° C.).

Workup

  1. customformed
  2. filtrationThe solution was filtered
  3. concentrationthe filtrate further concentrated

Sources & evidence

ORD record
ord-93d5f73e6f524122b892c1c8ee0c18de
Source dataset
uspto-grants-1996_09
Patent number
US05554542

Reaction notes

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