Water → HCID 54390691, compound
Reaction equation
[S:1](Cl)(=[O:4])(=[O:3])[NH2:2].[OH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1.C(N(CC)CC)C.O>C(Cl)Cl>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][O:6][S:1](=[O:4])(=[O:3])[NH2:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was obtained using the following procedure: The sulfamoyl chloride solution prepared in (a) was reacted as in Example 11 with 16.7 g (0.136 mole) of 2-(β-hydroxyethyl)pyridine using 54.9 g (0.544 mole) of triethylamine in 100 ml of methylene chloride. Water, 150 ml, was added to the reaction mixture with agitation and the layers were separated. The organic layer was discarded, pH of the aqueous layer was adjusted to 8 with sodium carbonate. The mixture was extracted with three 200 ml portions of methylene chloride. The organic extracts were washed twice with 200 ml portions of water, dried over magnesium sulfate and the solvent was evaporated under reduced pressure to give 7.1 g of a brown, viscous oil which solidified on standing. The solid was recrystallized from methylene chloride-petroleum ether (bp range 30°-60° C.) to give 3.2 g (12%) of title compound as white needles, mp 89°-91° C.
Workup
- customthe layers were separated
- extractionThe mixture was extracted with three 200 ml portions of methylene chloride
- washThe organic extracts were washed twice with 200 ml portions of water
- dry with materialdried over magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customto give 7.1 g of a brown, viscous oil which
- customThe solid was recrystallized from methylene chloride-petroleum ether (bp range 30°-60° C.)
Sources & evidence
- ORD record
- ord-18dd35af4f7c4004bca0815fa90fd36f
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05192785
Reaction notes
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