1,2-Ethanedithiol → 1-[4-(Mercaptoethylthio)phenyl]-2-methyl-2-morpholine-4-yl-propane-1-one

HRID 376956Notes

Reaction equation

[CH2:1]([SH:4])[CH2:2][SH:3].C(=O)([O-])[O-].[K+].[K+].F[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:28])[C:19]([CH3:27])([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH3:20])=[CH:14][CH:13]=1>CC(N(C)C)=O>[SH:3][CH2:2][CH2:1][S:4][C:12]1[CH:13]=[CH:14][C:15]([C:18](=[O:28])[C:19]([CH3:20])([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)[CH3:27])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 40 °C

Procedure

22.5 g (0.24 mol) of 1,2-ethanedithiol are dissolved in 70 ml of dry dimethylacetamide, 10.0 g of potassium carbonate are added and the solution is heated to about 40° C. 10.1 g o(0.04 mol) of 1-(4-fluorophenyl)-2-methyl-2-morpholine-4-yl-propane-1-one (prepared as described in example 1b) in 30 ml of dry dimethylacetamide are added dropwise. The suspension is stirred for 5 h, then the solid is filtered off and washed with toluene. From the filtrate the excess 1,2-ethanedithiol and toluene are distilled off. The residue is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as eluent. The resulting product has a melting point of 92-93° C. The structure is confirmed by the 1H-NMR-spectrum, measured in CDCl3. The signals (δ in ppm) are 1.31 (s,6H), 1.75 (t, 1H), 2.57 (t,4H), 2.80 (q,2H), 3.21 (t,2H), 3.70 (t,4H), 7.29 (d,2H), 8.51 (d,2H).

Workup

filtrationthe solid is filtered off
washwashed with toluene
distillationFrom the filtrate the excess 1,2-ethanedithiol and toluene are distilled off
customThe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (20:80) as eluent

Sources & evidence

ORD record: ord-bfa8744a87a040f4ad859cb83ff84d52
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022906

Reaction notes

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