Potassium Carbonate → Ethyl 2-(2-amino-4-thiazolyl)-2-propoxyiminoacetate

HRID 1577733Notes

Reaction equation

HRID 1577733 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[N:10][O:11][CH2:12][CH2:13][CH3:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[NH2:16][C:17]([NH2:19])=[S:18].O.C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O.C(O)C>[CH2:12]([O:11][N:10]=[C:4]([C:3]1[N:16]=[C:17]([NH2:19])[S:18][CH:2]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 23681166Acetic acid, sodium salt, monohydrateHCID 53923607Ethyl 4-chloro-3-oxo-2-(propoxyimino)butanoate

Product 1

HCID 53867037Ethyl 2-(2-amino-4-thiazolyl)-2-propoxyiminoacetateYield 62.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 4-chloro-3-oxo-2-n-propoxyiminobutyrate (syn isomer) (15.4 g.), thiourea (4.97 g.) and sodium acetate hydrate (8.89 g.) were dissolved in a mixture of water (40 ml.) and ethanol (50 ml.), and stirred at 40° C. for an hour. The reaction mixture was adjusted to pH 6.5 with a saturated aqueous solution of potassium carbonate under cooling and stirred at the same temperature for half an hour. The precipitating crystals were collected by filtration, washed with water and diisopropyl ether, and then dried to give crystalline ethyl 2-n-propoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetate (syn isomer) (10.55 g.), mp 142° to 144° C.

Workup

  1. temperatureunder cooling
  2. stirringstirred at the same temperature for half an hour
  3. filtrationThe precipitating crystals were collected by filtration
  4. washwashed with water and diisopropyl ether
  5. customdried

Sources & evidence

ORD record
ord-9f487019c2024eac9ce815778b9efba6
Source dataset
uspto-grants-1981_09
Patent number
US04288436

Reaction notes

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