HCID 22406946, compound → HCID 22406965, compound

HRID 440324Notes

Reaction equation

HRID 440324 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[OH:14][CH:15]([C:21]1[S:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:24][N:25]=1)[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]>CC(C)=O>[C:15]([C:21]1[S:22][C:23]([S:26]([NH2:29])(=[O:28])=[O:27])=[CH:24][N:25]=1)(=[O:14])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 22406946HCID 22406946, compoundHCID 131709961Jones' reagent

Product 1

HCID 22406965HCID 22406965, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (0.14 mL, 0.38 mmol, 2.67M) was added dropwise to a 0° C. solution of 2-(1-hydroxyhexyl)-5-thiazole sulfonamide (0.08 g, 0.32 mmol) in acetone (1 mL). The ice bath was removed and the solution stirred for 30 min. The reaction was quenched with a few drops of isopropanol and the acetone removed in vacuo. The residue was taken up in water and extracted with EtOAc. The combined extracts were dried (MgSO4), concentrated and recrystallized from EtOAc/hexane to give 0.031 g (38%) of 2-(1-hexanoyl)-5-thiazole sulfonamide as a white solid.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched with a few drops of isopropanol
  3. customthe acetone removed in vacuo
  4. extractionextracted with EtOAc
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. concentrationconcentrated
  7. customrecrystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-6cae32546d3c47948f42701b247f0629
Source dataset
uspto-grants-1996_05
Patent number
US05519040

Reaction notes

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