Chlorosulfonic acid → HCID 21555929, compound
Reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([NH:11][CH2:12][CH2:13][C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)(=[O:10])[CH2:7][CH2:8][CH3:9]>>[C:6]([NH:11][CH2:12][CH2:13][C:14]1[S:15][C:16]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:17][CH:18]=1)(=[O:10])[CH2:7][CH2:8][CH3:9]Participants
Procedure
6.6 ml (0.100 mol) of chlorosulphonic acid are cooled in an ice bath to 4°C whilst stirring, and 3.35 g (0.017 mol) of 2-(2-butyramido-ethyl)-thiophene are then added over the course of 15 minutes in such a way that the reaction temperature does not rise above 8°C. The ice bath is then removed and the reaction mixture is stirred for 30 minutes at 28°-30°C and then poured, whilst stirring, onto 100 g of ice under which there is a layer of 50 ml of methylene chloride. The methylene chloride phase is separated off and the aqueous phase is extracted with a further 50 ml of methylene chloride. The combined extracts are washed with 50 ml of concentrated sodium chloride solution, dried over sodium sulphate and evaporated at 40°C bath temperature with the aid of a rotary evaporator. The crude 5-(2-butyramido-ethyl)-2-thiophenesulphonyl chloride is obtained.
Workup
- customdoes not rise above 8°C
- customThe ice bath is then removed
- stirringthe reaction mixture is stirred for 30 minutes at 28°-30°C
- additionpoured
- stirringwhilst stirring, onto 100 g of ice under which there
- customThe methylene chloride phase is separated off
- extractionthe aqueous phase is extracted with a further 50 ml of methylene chloride
- washThe combined extracts are washed with 50 ml of concentrated sodium chloride solution
- dry with materialdried over sodium sulphate
- customevaporated at 40°C bath temperature
- customwith the aid of a rotary evaporator
Sources & evidence
- ORD record
- ord-4bcde65c6e7f4ab0af35bcd19ec5f8b2
- Source dataset
- uspto-grants-1976_03
- Patent number
- US03941804
Reaction notes
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