2-(Ethylthio)ethanol → HCID 67937194, compound

HRID 652422

Reaction equation

HRID 652422 reaction equation
[CH2:1]([O:10][C:11]([C:13]1[CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)[C:17]([C:28]([OH:30])=[O:29])=[C:16]([CH3:31])[NH:15][C:14]=1[CH3:32])=[O:12])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:48]([S:50][CH2:51][CH2:52]O)[CH3:49]>CN(C)C1C=CN=CC=1.ClC(Cl)C>[N+:25]([C:21]1[CH:20]=[C:19]([CH:18]2[C:17]([C:28]([O:30][CH2:49][CH2:48][S:50][CH2:51][CH3:52])=[O:29])=[C:16]([CH3:31])[NH:15][C:14]([CH3:32])=[C:13]2[C:11]([O:10][CH2:1][CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:12])[CH:24]=[CH:23][CH:22]=1)([O-:27])=[O:26]

Participants

6

Reactant 3

HCID 80752-(Ethylthio)ethanolHCID 10868DicyclohexylcarbodiimideHCID 70048882HCID 70048882, compound

Product 1

HCID 67937194HCID 67937194, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

434 mg (1 mM) of 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid monocinnamyl ester, 226 mg (1.1 mM) of dicyclohexylcarbodiimide, 122 mg (1 mM) of 4-dimethylaminopyridine and 127 mg (1.2 mM) of 2-ethylthioethanol were dissolved in 10 ml of dichloroethane, and refluxed for 2 hours. After the reaction mixture was chilled, insoluble matters were filtered off. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain 511 mg of cinnamyl 2-ethylthioethyl 4-(3-nitrophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (yield 98%).

Workup

  1. temperaturerefluxed for 2 hours
  2. temperatureAfter the reaction mixture was chilled
  3. filtrationinsoluble matters were filtered off
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3354f2b148ac433c8f8a8d029cfaacb4
Source dataset
uspto-grants-1987_06
Patent number
US04672068

Linked notes

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