Water → 2-Isopropyl-oxazole-4-carboxylic acid-cyclopropylamide

HRID 5331

Reaction equation

S(Cl)(Cl)=O.[CH:5]([C:8]1[O:9][CH:10]=[C:11]([C:13]([OH:15])=O)[N:12]=1)([CH3:7])[CH3:6].[CH:16]1([NH2:19])[CH2:18][CH2:17]1.O>C1(C)C=CC=CC=1.CN(C)C=O.ClCCl>[CH:16]1([NH:19][C:13]([C:11]2[N:12]=[C:8]([CH:5]([CH3:6])[CH3:7])[O:9][CH:10]=2)=[O:15])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 80 °C

Procedure

At room temperature, 47.6 g (0.40 mol) of thionyl chloride was dripped into a solution of 31.0 g (0.20 mol) of 2-isopropyloxazole-4-carboxylic acid in 200 ml of toluene and 2 ml of dimethylformamide, and the mixture was stirred for one hour at 80° C. The solvents were stripped off under reduced pressure, the residue was dissolved in 300 ml of dichloromethane, and 24.0 g (0.42 mol) of cyclopropylamine in 20 ml of dichloromethane was dripped in at 0° to 10° C. The mixture was stirred for 12 hours at room temperature, 150 ml of water was added, the phases were separated, the organic phase was washed once with saturated sodium bicarbonate solution and dried over magnesium sulfate, and the solvent was removed under reduced pressure. There was obtained 37.2 g (96%) of 2-isopropyl-oxazole-4-carboxylic acid-cyclopropylamide.

Workup

customAt room temperature
customwas dripped in at 0° to 10° C
stirringThe mixture was stirred for 12 hours at room temperature
customthe phases were separated
washthe organic phase was washed once with saturated sodium bicarbonate solution
dry with materialdried over magnesium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-7521a5ff0c9d4c75bde504a8fa790722
Source dataset: uspto-grants-1993_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05244867

Linked notes

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