Ethanol → N,N'-Dicyclohexylurea

HRID 358109Notes

Reaction equation

HRID 358109 reaction equation
C(CC(OC1C=[C:10]([C:14]2[N:15]=[C:16]3[N:20]([CH:21]=2)[C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2S3)[CH:11]=[CH:12][CH:13]=1)=O)(O)=O.C([OH:28])C.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH:19]1([NH:20][C:16]([NH:15][CH:14]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:21]2)=[O:28])[CH2:18][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 1373073-[3-(Imidazo[2,1-b][1,3]benzothiazol-2-yl)phenoxy]-3-oxopropanoic acid

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4 g of 2-(m-carboxyacetoxyphenyl)imidazo[2,1-b]benzothiazole, 0.52 g of ethanol, and 50 ml of tetrahydrofuran was added a mixture of 2.3 g of dicyclohexylcarbodiimide and 10 ml of tetrahydrofuran at a temperature below 10° C. Thereafter, the mixture was stirred overnight at room temperature. Dicyclohexyl urea thus formed was filtered off and the filtrate was concentrated under reduced pressure. The residue was applied to silica gel column chromatography (80 ml of silica gel, eluate: a mixture of toluene and ethyl acetate (9:1)) to provide 2.0 g of oily 2-(m-ethoxycarbonylacetoxyphenyl)imidazo[2,1-b]benzothiazole.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-d527bffdb09447ec874148bbd199ad2e
Source dataset
uspto-grants-1984_08
Patent number
US04464384

Reaction notes

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