Morpholine → trans-2-(3-(2-Morpholinoethylsulfonyl)-4-propoxy-5-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

HRID 1684048Notes

Reaction equation

HRID 1684048 reaction equation
O[CH2:2][CH2:3][S:4]([C:7]1[CH:8]=[C:9]([C@H:19]2[S:23][C@H:22]([C:24]3[CH:29]=[C:28]([O:30][CH3:31])[C:27]([O:32][CH3:33])=[C:26]([O:34][CH3:35])[CH:25]=3)[CH2:21][S:20]2)[CH:10]=[C:11]([O:17][CH3:18])[C:12]=1[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5].[NH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>C(O)C>[O:39]1[CH2:40][CH2:41][N:36]([CH2:2][CH2:3][S:4]([C:7]2[CH:8]=[C:9]([C@H:19]3[S:23][C@H:22]([C:24]4[CH:25]=[C:26]([O:34][CH3:35])[C:27]([O:32][CH3:33])=[C:28]([O:30][CH3:31])[CH:29]=4)[CH2:21][S:20]3)[CH:10]=[C:11]([O:17][CH3:18])[C:12]=2[O:13][CH2:14][CH2:15][CH3:16])(=[O:6])=[O:5])[CH2:37][CH2:38]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 86750981trans-2-(3-(2-Hydroxyethylsufonyl)-5-methoxy-4-propoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

Product 1

HCID 86750982trans-2-(3-(2-Morpholinoethylsulfonyl)-4-propoxy-5-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(3-(vinylsufonyl)-5-methoxy-4-propoxyphenyl)-4-(3,4,5-methoxyphenyl)-1,3-dithiolane (22) (FIG. 25) (0.040 g,0.076 mmole) was dissolved in absolute ethanol (10 ml) and morpholine (13 ml) was into the reaction which was stirred at room temperature for 4 hours. The solvent and excess amine were removed in vacuo, and the remaining oil purified by flash column chromatography with 1:1 hex/ethyl acetate as eluent. The product mixture (oil) contains a 1.0/1.0 cis/trans ratio (0.022.5 g, 49%).

Workup

  1. customThe solvent and excess amine were removed in vacuo
  2. customthe remaining oil purified by flash column chromatography with 1:1 hex/ethyl acetate as eluent

Sources & evidence

ORD record
ord-683f412d751b40ed88e46c0cb308aac3
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

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