HCID 11153426, compound → HCID 19842251, compound

HRID 280540Notes

Reaction equation

HRID 280540 reaction equation
O[CH:2]1[C:6]2[S:7][CH2:8][CH2:9][S:10][C:5]=2[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.[N:20]1([C:26]([CH:28]=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([N:3]2[C:4](=[O:11])[C:5]3[S:10][CH2:9][CH2:8][S:7][C:6]=3[CH:2]2[CH2:28][C:26]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[O:27])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 11153426HCID 11153426, compoundHCID 19842209HCID 19842209, compound

Product 1

HCID 19842251HCID 19842251, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3,6,7-Tetrahydro-7-hydroxy-6-(4-methoxyphenyl)-5H-1,4-dithiino[2,3-C]pyrrol-5-one (1.48 g) and piperidinocarbonylmethylenetriphenylphosphorane (3.4 g) were dissolved in toluene (30 ml) under heating, and the solution was refluxed for 12 hours. The reaction mixture was concentrated and the residue was subjected to silica gel column chromatography (methylene chloride:ethyl acetate=10:1). The thus-obtained crude crystals were recrystallized from ethyl acetate-ether to give crystals (1.45 g) of 2,3,6,7-tetrahydro-6-(4-methoxyphenyl)-7-piperidinocarbonylmethyl-5H-1,4-dithiino[2,3-C]pyrrol-5-one, melting at 163°-164° C. and 183°-185° C. (double melting).

Workup

  1. temperatureunder heating
  2. temperaturethe solution was refluxed for 12 hours
  3. concentrationThe reaction mixture was concentrated
  4. customThe thus-obtained crude crystals
  5. customwere recrystallized from ethyl acetate-ether

Sources & evidence

ORD record
ord-33df2781dce543d1b9e4f793f3c373c4
Source dataset
uspto-grants-1986_05
Patent number
US04590189

Reaction notes

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