Hydrochloric Acid → 2-(2-Formamido-5-chlorothiazol-4-yl)-2-propargyloxyiminoacetic acid
Reaction equation
[Cl:1]Cl.[CH:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:15][O:16][CH2:17][C:18]#[CH:19])[C:12]([OH:14])=[O:13])[N:10]=1)=[O:4].C(=O)(O)[O-].[Na+].[OH-].[Na+].Cl>C(O)(=O)C.C(Cl)(Cl)Cl>[CH:3]([NH:5][C:6]1[S:7][C:8]([Cl:1])=[C:9]([C:11](=[N:15][O:16][CH2:17][C:18]#[CH:19])[C:12]([OH:14])=[O:13])[N:10]=1)=[O:4]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of chlorine (3.2 g) in acetic acid (44 ml) was dropwise added to a solution of 2-(2-formamidothiazol-4-yl)-2-(propargyloxyimino)acetic acid (syn isomer) (10 g) in chloroform (250 ml) at 0° C., and the mixture was stirred for 30 minutes at same temperature. The resultant solution was added to a saturated aqueous solution of sodium bicarbonate and adjusted to pH 7.5 with 10% aqueous solution of sodium hydroxide. The separated aqueous layer was adjusted to pH 2.0 with conc. hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was washed with diisopropyl ether and collected by filtration to give 2-(2-formamido-5-chlorothiazol-4-yl)-2-propargyloxyiminoacetic acid (syn isomer) (5.96 g), mp 161° to 162° C. (dec.).
Workup
- extractionextracted with ethyl acetate
- washThe extract was washed with a saturated aqueous solution of sodium chloride
- dry with materialdried over magnesium sulfate
- customevaporated in vacuo
- washThe residue was washed with diisopropyl ether
- filtrationcollected by filtration
Sources & evidence
- ORD record
- ord-49c7b3880973495c809886b3b2c3f169
- Source dataset
- uspto-grants-1986_06
- Patent number
- US04596829
Reaction notes
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