Hydrochloric Acid → Ethyl 2-{4-[2-(6-[(3-chlorophenyl)(methoxyimino)methyl]-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoate

HRID 1790269Notes

Reaction equation

HRID 1790269 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[C:5]([C:7]1[CH:34]=[CH:33][C:10]2[N:11]([CH2:15][CH2:16][O:17][C:18]3[CH:32]=[CH:31][C:21]([O:22][C:23]([CH3:30])([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:20][CH:19]=3)[C:12](=[O:14])[S:13][C:9]=2[CH:8]=1)=O.Cl.[CH3:39][O:40][NH2:41].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:5](=[N:41][O:40][CH3:39])[C:7]2[CH:34]=[CH:33][C:10]3[N:11]([CH2:15][CH2:16][O:17][C:18]4[CH:19]=[CH:20][C:21]([O:22][C:23]([CH3:29])([CH3:30])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:31][CH:32]=4)[C:12](=[O:14])[S:13][C:9]=3[CH:8]=2)[CH:35]=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 521874O-Methylhydroxylamine hydrochlorideHCID 22041531Ethyl 2-{4-[2-(6-(3-chlorobenzoyl)-2-oxo-1,3-benzothiazol-3(2H)-yl)-ethoxy]phenoxy}-2-methylpropanoate

Product 1

HCID 86760134Ethyl 2-{4-[2-(6-[(3-chlorophenyl)(methoxyimino)methyl]-2-oxo-1,3-benzothiazol-3(2H)-yl)ethoxy]phenoxy}-2-methylpropanoate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of the compound obtained in Step A (1.00 g) and O-methylhydroxylamine hydrochloride (309 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 and acidified using 6N HCl. The precipitate obtained is filtered off, washed with water and then recrystallised from petroleum ether by cooling in a freezer 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 filtered off
  4. washwashed with water
  5. customrecrystallised from petroleum ether
  6. temperatureby cooling in a freezer

Sources & evidence

ORD record
ord-43e233c2fe6e4d73b14262eec7767f6c
Source dataset
uspto-grants-2006_07
Patent number
US07071221B2

Reaction notes

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