Methanol → 2-(2-Aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acid

HRID 364500Notes

Reaction equation

HRID 364500 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][Cl:17])[C:8]([O:10]CC)=[O:9])[N:6]=1.[OH-].[Na+].CO>O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][Cl:17])[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53650816Ethyl 2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetate

Product 1

HCID 538294892-(2-Aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetic acidYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)acetate (syn isomer, 30.5 g.), 1N aqueous solution of sodium hydroxide (220 ml.), methanol (110 ml.) and tetrahydrofuran (140 ml.) were treated in a similar manner to that of Example F-(4) to give 2-(2-aminothiazol-4-yl)-2-(2-chloroethoxyimino)-acetic acid (syn isomer, 23.4 g.), mp 201° C. (dec.).

Sources & evidence

ORD record
ord-d07fd46a1efd4490a068cbc70eb811dd
Source dataset
uspto-grants-1986_08
Patent number
US04604456

Reaction notes

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