2-(Dimethylamino)ethanol → 2-[3-(2-Dimethylaminoethoxy)propyl]-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole

HRID 2351004Notes

Reaction equation

[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].[H-].[Na+].Br[CH2:10][CH2:11][CH2:12][CH:13]1[S:17][C:16]2[C:18]([CH3:28])=[C:19]([O:24][CH2:25][O:26][CH3:27])[C:20]([CH3:23])=[C:21]([CH3:22])[C:15]=2[O:14]1>CS(C)=O>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][CH2:10][CH2:11][CH2:12][CH:13]1[S:17][C:16]2[C:18]([CH3:28])=[C:19]([O:24][CH2:25][O:26][CH3:27])[C:20]([CH3:23])=[C:21]([CH3:22])[C:15]=2[O:14]1

Participants

Conditions

Temperature: 50 °C

Procedure

740 mg of 2-dimethylaminoethanol were dissolved in 10 ml of dimethyl sulfoxide, and 220 mg of a 50% w/w oily suspension of sodium hydride was added to the resulting solution; the reaction mixture was then heated at 50° C. for 1 hour, after which it was cooled down with ice, and a solution of 1.68 g of 2-(3-bromopropyl)-5-methoxymethoxy-4,6,7-trimethyl-1,3-benzoxathiole (prepared as described in Example 87) in 5 ml of dimethyl sulfoxide was added dropwise, while stirring. The reaction product was then subjected to the same reaction process, extraction and separation procedures as described in (a) above, to give the title compound with the same Rf value and mass spectrum as those of the product obtained in (a).

Workup

additionwas added to the resulting solution
temperatureafter which it was cooled down with ice
extractionThe reaction product was then subjected to the same reaction process, extraction and separation procedures

Sources & evidence

ORD record: ord-919d7175fcdf485cacaea0bc701bd68c
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04871762

Reaction notes

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