Hydrochloric Acid → 2-(2-Formamido-5-chlorothiazol-4-yl)-2-propargyloxyiminoacetic acid
Reaction equation
[Cl:1]Cl.[CH2:3]([O:6][N:7]=[C:8]([C:12]1[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=1)[C:9]([OH:11])=[O:10])[C:4]#[CH:5].C(=O)(O)[O-].[Na+].[OH-].[Na+].Cl>C(O)(=O)C.C(Cl)(Cl)Cl>[CH2:3]([O:6][N:7]=[C:8]([C:12]1[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][C:16]=1[Cl:1])[C:9]([OH:11])=[O:10])[C:4]#[CH:5]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of chlorine (3.2 g) in acetic acid (44 ml) was added dropwise to a solution of 2-(2-propynyloxyimino)-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer)(10 g) in chloroform (250 ml) at 0° C. and the mixture was stirred for 30 minutes at the same temperature. The resulting solution was added to a saturated aqueous sodium bicarbonate and the mixture was adjusted to pH 7.5 with 10% aqueous sodium hydroxide. The separated aqueous layer was adjusted to pH 2.0 with conc. hydrochloric acid and extracted with ethyl acetate. The extracts were washed with a saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated. The residue was washed with diisopropyl ether and filtered to give 2-(2-propynyloxyimino)-2-(2-formamido-5-chlorothiazol-4-yl)acetic acid (syn isomer)(5.96 g), mp 161°-162° C. (dec.).
Workup
- extractionextracted with ethyl acetate
- washThe extracts were washed with a saturated aqueous sodium chloride
- dry with materialdried over magnesium sulfate
- customevaporated
- washThe residue was washed with diisopropyl ether
- filtrationfiltered
Sources & evidence
- ORD record
- ord-909fe8c2800642faaf94660f2d819ea7
- Source dataset
- uspto-grants-1984_01
- Patent number
- US04427677
Reaction notes
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