Methanol → 2-(2-Aminothiazol-4-yl)-2-(2,4-dichlorobenzyloxyimino)acetic acid

HRID 1758397Notes

Reaction equation

HRID 1758397 reaction equation
CN1C=CN=C1.[NH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[C:14]([O:16]CC)=[O:15])[N:12]=1.CO.O1CCCC1>[OH-].[Na+]>[NH2:7][C:8]1[S:9][CH:10]=[C:11]([C:13](=[N:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=2[Cl:29])[C:14]([OH:16])=[O:15])[N:12]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 13901-MethylimidazoleHCID 8028TetrahydrofuranHCID 54440018Ethyl 2-(2-aminothiazol-4-yl)-2-(2,4-dichlorobenzyloxyimino)acetate

Product 1

HCID 540764532-(2-Aminothiazol-4-yl)-2-(2,4-dichlorobenzyloxyimino)acetic acidYield 90.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 1-methylimidazole (0.5 g.) in 1 N sodium hydroxide aqueous solution (48 ml.) was added to a solution of ethyl 2-(2-aminothiazol-4-yl)-2-(2,4-dichorobenzyloxyimino)acetate (syn isomer, 12.0 g.), methanol (120 ml.) and tetrahydrofuran (100 ml.) at 15° to 20° C., and stirred at 35° to 40° C. for 6 hours. After removing methanol and tetrahydrofuran in vacuo from the resultant mixture, the aqueous residue was washed with ethyl acetate. Ethyl acetate was completely removed from the aqueous solution and adjusted to pH 2.0 with hydrochloric acid. The precipitates were collected by filtration to give 2-(2-aminothiazol-4-yl)-2-(2,4-dichlorobenzyloxyimino)acetic acid (syn isomer, 10.0 g.).

Workup

  1. customAfter removing methanol and tetrahydrofuran in vacuo from the resultant mixture
  2. washthe aqueous residue was washed with ethyl acetate
  3. customEthyl acetate was completely removed from the aqueous solution
  4. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-24a7d1cce7594c86839bb70031a79d3b
Source dataset
uspto-grants-1983_02
Patent number
US04372952

Reaction notes

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