Dimethyl Sulfoxide → N,N'-Dicyclohexylurea

HRID 1449225Notes

Reaction equation

HRID 1449225 reaction equation
BrC1C=CC([O:6]CC(O)C)=CC=1.CS(C)=O.[CH:17]1([N:23]=[C:24]=[N:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.FC(F)(F)C(O)=O.C(O)(=O)C(O)=O>CCOCC.CO.N1C=CC=CC=1>[CH:26]1([NH:25][C:24](=[O:6])[NH:23][CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

9

Reactant 5

HCID 679Dimethyl SulfoxideHCID 971Oxalic AcidHCID 6422Trifluoroacetic acidHCID 10868Dicyclohexylcarbodiimide2×HCID 12384825HCID 12384825, compound

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution is prepared from 43.35 g (0.1 mol) 3-[2-(2-propinoxycarbonyl)-ethyl]-phenoxy)-1-(4'-bromophenoxy)-propane-2-ol in 500 ml absolute ether and mixed at room temperature with 40 mol dimethylsulfoxide, 7 ml pyridine and 30.95 g (0.15 mol) dicyclohexylcarbodiimide. After adding 5 ml trifluoroacetic acid, the mixture is stirred until no starting compound can be determined through thin-layer chromatographic control. In order to eliminate excessive dicyclohexylcarbodiimide, the reaction mixture is mixed in portions with a solution of 30 g oxalic acid in methanol and stirred for 20 minutes. After the dicyclohexyl-urea precipitate formed is separated, the filtrate is washed with a solution of sodium hydrocarbonate and then with water. The organic phase is dried over sodium sulfate and concentrated in vacuo. The raw product is recrystallized twice. Colorless crystals, melting point 90°-1° C. (isopropanol): yield 37.56 g (87.1%).

Workup

  1. stirringstirred for 20 minutes

Sources & evidence

ORD record
ord-eff7c6053ed04926adfee7db2b787651
Source dataset
uspto-grants-1980_02
Patent number
US04189594

Reaction notes

Loading…