Hydrochloric Acid → Ethyl 2-{4-[2-(6 [(hydroxyimino)(phenyl)methyl]-2-oxo-1,3-benzo-thiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoate

HRID 1790265Notes

Reaction equation

HRID 1790265 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.[NH2:38][OH:39].Cl>N1C=CC=CC=1>[OH:39][N:38]=[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:34]=[CH:33][C:23]([O:24][C:25]([CH3:31])([CH3:32])[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

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 22041523Ethyl 2-{4-[2-(6-benzoyl-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoate

Product 1

HCID 86596384Ethyl 2-{4-[2-(6 [(hydroxyimino)(phenyl)methyl]-2-oxo-1,3-benzo-thiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the compound obtained in Step A of Example 31 (500 mg) and hydroxylamine hydrochloride (137 mg) in 10 ml of pyridine is heated at reflux for 3 hours. The reaction mixture is hydrolysed using 100 ml of ice-cold water and is acidified using 6N HCl. The precipitate obtained is then filtered off, washed with water and then with petroleum ether and purified on silica gel (eluant AcOEt/PE 2/8) to yield the title compound in the form of a white powder.

Workup

  1. temperatureat reflux for 3 hours
  2. customThe precipitate obtained
  3. filtrationis then filtered off
  4. washwashed with water
  5. customwith petroleum ether and purified on silica gel (eluant AcOEt/PE 2/8)

Sources & evidence

ORD record
ord-f46bba6eaa754bbfac2c0e0b61e99bc0
Source dataset
uspto-grants-2006_07
Patent number
US07071221B2

Reaction notes

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