Water → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-(diethylamino)-2-oxoethoxy]iminoacetic acid

HRID 1195069Notes

Reaction equation

HRID 1195069 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])/[C:8]([O:10]CC)=[O:9])[N:6]=1.O.[OH-].[Na+]>CO>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH2:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 21269044HCID 21269044, compound

Product 1

HCID 21269034(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-(diethylamino)-2-oxoethoxy]iminoacetic acidYield 402.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

68.1 g of ethyl 2-(2-amino-4-thiazolyl)-2-[(Z)-[(diethylcarbamoyl)methoxy]imino]-acetate are dissolved in 2.8 l of methanol and 240 ml of water and the solution is treated with 230 ml of 1N aqueous sodium hydroxide solution. The methanol is removed under reduced pressure after 48 hours and the aqueous solution is washed with ethyl acetate. After the addition of 230 ml of 1N aqueous hydrochloric acid, the crystallized acid is filtered off and dried. There are obtained 250.8 g of 2-(2-amino-4-thiazolyl)-2-[(Z)-[(diethylcarbamoyl)methoxy]imino]-acetic acid of melting point 180° C.

Workup

  1. customThe methanol is removed under reduced pressure after 48 hours
  2. washthe aqueous solution is washed with ethyl acetate
  3. additionAfter the addition of 230 ml of 1N aqueous hydrochloric acid
  4. filtrationthe crystallized acid is filtered off
  5. customdried

Sources & evidence

ORD record
ord-5730ed26a10b48a099a3cbc4a33b42f2
Source dataset
uspto-grants-1989_03
Patent number
US04816582

Reaction notes

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