Sodium Carbonate → HCID 23342963, compound

HRID 2057578Notes

Reaction equation

[C:1]1([C:7]2[CH2:11][CH:10]([C:12]([OH:14])=[O:13])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:21]([S:24][CH2:25][CH2:26][C:27](Cl)=[O:28])(=[O:23])[CH3:22]>O.C(OCC)(=O)C>[C:21]([S:24][CH2:25][CH2:26][C:27]([N:9]1[CH:10]([C:12]([OH:14])=[O:13])[CH2:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8]1)=[O:28])(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 5 °C

Procedure

A suspension of 8.0 g of 4,5-dihydro-3-phenyl-1H-pyrazole-5-carboxylic acid in 200 ml of distilled water is treated slowly with 2.6 g of sodium carbonate. The solution is layered with 50 ml of ethyl acetate, cooled to 5° C. and treated with 7.0 g of 3-(acetylthio)propionyl chloride in 10 ml of ethyl acetate. The pH of the reaction mixture is maintained at 7.5-8.0 by the addition of concentrated sodium carbonate solution. The mixture is stirred at room temperature for 30 minutes. The ethyl acetate layer is then discarded and the aqueous layer is washed twice with fresh ethyl acetate. Using 6 N hydrochloric acid, the pH of the aqueous layer is adjusted to 2.5 and then it is extracted with two 100 ml portions of ethyl acetate. The combined extracts are dried over magnesium sulfate and concentrated to a point where precipitation begins. Cooling affords 10.6 g of the title compound, melting point 137°-139° C.

Workup

washthe aqueous layer is washed twice with fresh ethyl acetate
extractionit is extracted with two 100 ml portions of ethyl acetate
dry with materialThe combined extracts are dried over magnesium sulfate
concentrationconcentrated to a point where precipitation
temperatureCooling

Sources & evidence

ORD record: ord-e980837ac0344dfc85a215f4c76e4c68
Source dataset: uspto-grants-1980_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04211786

Reaction notes

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