1,3-Propanedithiol → HCID 18755074, compound

HRID 376960Notes

Reaction equation

[CH2:1]([SH:5])[CH2:2][CH2:3][SH:4].C(=O)([O-])[O-].[K+].[K+].F[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:28])[C:20]([N:25]([CH3:27])[CH3:26])([CH3:24])[CH2:21][CH:22]=[CH2:23])=[CH:15][CH:14]=1>CC(N(C)C)=O>[SH:4][CH2:3][CH2:2][CH2:1][S:5][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:28])[C:20]([N:25]([CH3:27])[CH3:26])([CH3:24])[CH2:21][CH:22]=[CH2:23])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

25.0 g (0.23 mol) of 1,3-propandithiol are dissolved in 80 ml of dry dimethylacetamide and 6.0 g of potassium carbonate are added. 10.0 g of 1-(4-fluorophenyl)-2-dimethylamino-2-methylpent-4-en-1-one in 20 ml of dry dimethylacetamide are added dropwise. The suspension is stirred at 50° C. for 12 h, the solid is filtered off. The excess 1,3-propanedithiol and dimethylacetamide are distilled off. To the residue toluene is added and the precipitate is filtered off. After toluene is distilled off, the residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:10) as eluent and an oily product is obtained. The structure is confirmed by the 1H-NMR-spectrum, measured in CDCl3. The signals (δ in ppm) are 1.18 (s,3H), 1.39 (t,1H), 2.00 (m,2H), 2.27 (s,5H), 2.42 (m, 1H), 2.66-2.72 (m,3H), 3.12 (t,2H), 4.83-4.93 (m,2H), 5.52 (m, 1H), 7.26 (d,2H), 8.38 (d,2H).

Workup

filtrationthe solid is filtered off
distillationThe excess 1,3-propanedithiol and dimethylacetamide are distilled off
additionTo the residue toluene is added
filtrationthe precipitate is filtered off
distillationAfter toluene is distilled off
customthe residue is purified by column chromatography on silica gel with ethyl acetate-hexane (1:10) as eluent
customan oily product is obtained

Sources & evidence

ORD record: ord-95ce2a481a57419a877e68bd71e9f7b9
Source dataset: uspto-grants-2000_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06022906

Reaction notes

Loading…