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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 399638Generated: November 1, 2026

Methanol → 4-(2,4-dihydroxymethylphenyl)-5-methyl-2-[N-(alpha-cycloproplybenzyl)-N-propylamino]thiazole

https://huagongshe.com/reaction/399638

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantBoraneHCID 6331—
ReactantPotassium CarbonateHCID 11430—
Reactant4-(2,4-dicarboxyphenyl)-5-methyl-2-[N-(alpha-cyclopropylbenzyl)-N-propylamino]thiazoleHCID 18967803—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product4-(2,4-dihydroxymethylphenyl)-5-methyl-2-[N-(alpha-cycloproplybenzyl)-N-propylamino]thiazoleHCID 15291621—

Reaction Conditions

Temperature60 °C

Reaction Steps

1 g of the compound obtained in Step A is dissolved in 20 ml of anhydrous tetrahydrofuran, followed, at -7° C., by addition of 5 ml of 1M borane solution in tetrahydrofuran, and the mixture is stirred overnight. 0.5 g of potassium carbonate and 10 ml of a mixture of methanol and water (1:1 v/v) are then added. The mixture is maintained at 60° C. for 2 hours and then cooled and evaporated under vacuum. The residue is taken up in water and extracted with ethyl ether, and the organic phase is washed with water, then with saturated aqueous sodium chloride and dried over anhydrous sodium sulphate. It is evaporated to dryness and the residue is taken up in pentane. The expected product is thus obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05821255
Source datasetuspto-grants-1998_10
ORD IDord-ea83c9ff24a245f2b6a63b23862af4bd
Source noteuspto-grants-1998_10