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

HRID 745394Notes

Reaction equation

HRID 745394 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 1N sodium hydroxide aqueous solution (48 ml.) was added to a solution of ethyl 2-(2-aminothiazol-4-yl)-2-(2,4-dichlorobenzyloxyimino)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-bcce3adec8a748a6947d99debc970ef8
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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