Hydrochloric Acid → HCID 86596385, compound

HRID 1790264Notes

Reaction equation

HRID 1790264 reaction equation
[C:1]([C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:17][CH2:18][O:19][C:20]3[CH:34]=[CH:33][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=3)[C:14](=[O:16])[S:15][C:11]=2[CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:38][O:39][NH2:40].Cl>N1C=CC=CC=1>[CH3:38][O:39][N:40]=[C:1]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[CH:36]=[CH:35][C:12]2[N:13]([CH2:17][CH2:18][O:19][C:20]3[CH:21]=[CH:22][C:23]([O:24][C:25]([CH3:32])([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:33][CH:34]=3)[C:14](=[O:16])[S:15][C:11]=2[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 521874O-Methylhydroxylamine hydrochlorideHCID 22041523Ethyl 2-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoate

Product 1

HCID 86596385HCID 86596385, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the compound obtained in Step A (500 mg) and O-methylhydroxylamine hydrochloride (165 mg) in 15 ml of pyridine is heated at reflux for 3 hours. The reaction mixture is hydrolysed using 100 ml of ice-cold water, acidified using 6N HCl and then extracted with ethyl acetate. The organic phase is dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue is then purified on silica gel, eluant AcOEt/PE 2/8, to yield the title compound in the form of a white oil (wax).

Workup

  1. temperatureat reflux for 3 hours
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is then purified on silica gel, eluant AcOEt/PE 2/8

Sources & evidence

ORD record
ord-b5f77654d99d40ec94ce5c7a18edac57
Source dataset
uspto-grants-2006_07
Patent number
US07071221B2

Reaction notes

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