Potassium Carbonate → HCID 13536830, compound

HRID 414799Notes

Reaction equation

HRID 414799 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[OH:14])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:22]1[CH2:26][CH2:25][NH:24][C:23]1=[O:27]>CS(C)=O.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][CH:22]2[CH2:26][CH2:25][NH:24][C:23]2=[O:27])/[C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetateHCID 101034713-Bromopyrrolidin-2-one

Product 1

HCID 13536830HCID 13536830, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

10.9 g of ethyl (Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate are dissolved in 25 ml of dimethylsulfoxide, and a solution of 14 g of anhydrous potassium carbonate in 13 ml of water is added thereto at a temperature of 15° to 20° C. The mixture is stirred at the same temperature for 20 minutes. 10 g of 3-bromo-2-pyrrolidone are added to said mixture at room temperature, and the mixture is stirred at the same temperature for 1.5 hours. 120 ml of water are added to the reaction mixture, and the aqueous mixture is stirred with ice-cooling. Crystalline precipitates are collected by filtration, and the crystals are washed with water and then dried at 40° C. 13 g of ethyl (Z)-2-(2-aminothiazol-4-yl)-2-[(2-pyrrolidon-3yl)oxyimino]acetate are obtained. The physico-chemical properties of this product are identical sith those of the product obtained in Example 2-(3).

Workup

  1. customat a temperature of 15° to 20° C
  2. customat room temperature
  3. stirringthe mixture is stirred at the same temperature for 1.5 hours
  4. stirringthe aqueous mixture is stirred with ice-
  5. temperaturecooling
  6. customCrystalline precipitates
  7. filtrationare collected by filtration
  8. washthe crystals are washed with water
  9. customdried at 40° C

Sources & evidence

ORD record
ord-6387dcdd172940d5bd1c97f21005facf
Source dataset
uspto-grants-1988_12
Patent number
US04794186

Reaction notes

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