Water → HCID 19956155, compound

HRID 1779433Notes

Reaction equation

HRID 1779433 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]([CH3:11])([CH3:10])[C:7](O)=[O:8].[NH2:12][C:13]1[S:14][C:15]([C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])=[N:16][N:17]=1.O>CN(C)C(=O)C>[C:20]1([C:18]([C:15]2[S:14][C:13]([NH:12][C:7](=[O:8])[C:6]([OH:5])([CH3:11])[CH3:10])=[N:17][N:16]=2)=[O:19])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 116712-Hydroxyisobutyric acidHCID 24386Thionyl ChlorideHCID 12229985HCID 12229985, compound

Product 1

HCID 19956155HCID 19956155, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
-10 °C

Procedure

Thionyl chloride (60 μl, 0.82 mmol) is added to 2-hydroxyisobutyric acid (82.9 mg, 0.796 mmol) in 5.0 ml of N,N-dimethylacetamide at -20°/-15° C. and the mixture is stirred at -15°/-10° C. for one hour. After adding 2-amino-5-(phenylcarbonyl)-1,3,4-thiadiazole (97.5 mg, 0.475 mmol) and equilibrating the reaction mixture to room temperature, it is stirred overnight. The reaction mixture is poured into 75 ml of water and subjected to extraction with 3×25 ml of ethyl acetate. The combined organic phases are dried over magnesium sulfate and filtered and the solvent is distilled off. The oil which remains is purified by flash chromatography (eluent: 33.% v/v ethyl acetate in petroleum ether (40/60)).

Workup

  1. customto room temperature
  2. stirringit is stirred overnight
  3. extractionsubjected to extraction with 3×25 ml of ethyl acetate
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. filtrationfiltered
  6. distillationthe solvent is distilled off
  7. customThe oil which remains is purified by flash chromatography (eluent: 33.% v/v ethyl acetate in petroleum ether (40/60))

Sources & evidence

ORD record
ord-ae1225f70ad14defaaeedd95c20fe267
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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