Triethylamine → Ethyl 2-(phenylsulfanyl)ethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1645969Notes

Reaction equation

HRID 1645969 reaction equation
[C:1]1([S:7][CH2:8][CH2:9][O:10][C:11](=[O:16])[CH2:12][C:13](=O)[CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:17]=[C:18]1[O:22][C:20](=[O:21])[CH2:19]1.O[CH2:24][CH2:25]SC1C=CC=CC=1.[CH2:33]([N:35](CC)CC)[CH3:34]>>[C:1]1([S:7][CH2:8][CH2:9][O:10][C:11]([C:12]2[CH:24]([CH3:25])[C:19]([C:20]([O:22][CH2:18][CH3:17])=[O:21])=[C:33]([CH3:34])[NH:35][C:13]=2[CH3:14])=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 12661DiketeneHCID 696852-(Phenylthio)ethanolHCID 13861151HCID 13861151, compound

Product 1

HCID 133736Ethyl 2-(phenylsulfanyl)ethyl 2,4,6-trimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Conditions

Temperature
80 °C

Procedure

2-(phenylthio)ethyl-acetylacetate 28.5 ml (31.24 g, 0.37 moles) of diketene are added drop by drop and with stirring to a mixture made up of 50 ml (57.30 g; 0.37 moles) of 2-hydroxyethylphenylsulfide and 0.4 ml triethylamine previously heated to 80° C. The rate of addition is adjusted so that the temperature is kept between 85°-90° C. Once the adding has ended the reaction mixture is kept at 90° C. for 3 hours with stirring. The desired product is isolated by reduced pressure distillation of the previous mixture, resulting in a colorless liquid; melting point: 143°-5° C./0.5 Torr. The yield of the reaction is 86%.

Workup

  1. additionThe rate of addition
  2. customis kept between 85°-90° C
  3. stirringwith stirring

Sources & evidence

ORD record
ord-95ea4ca9d4994459bd67b60f1235ee70
Source dataset
uspto-grants-1993_01
Patent number
US05177211

Reaction notes

Loading…