Triethylamine → HCID 65482176, compound
Reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH:13]1([NH2:16])[CH2:15][CH2:14]1.C(N(CC)CC)C>ClCCl>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:16][CH:13]2[CH2:15][CH2:14]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
5 g of 4-(bromomethyl)benzenesulfonyl chloride (18.6 mmol, 1 eq.) were dissolved under argon atmosphere in 82.5 ml of dichloromethane and cooled down at −10° C. internal temperature. A solution of 1.29 ml cyclopropanamine (18.6 mmol, 1 eq.) and 2.59 ml of triethylamine (18.6 mmol, 1 eq.) in 82.5 ml of dichloromethane were added dropwise at −10° C. internal temperature and stirred at this temperature for one hour. The reaction mixture was washed once with 1 M aqueous hydrogen solution and twice with distilled water. The organic layer was dried over sodium sulfate and concentrated in vacuo. The crude product contained a mixture of bromomethyl- and chloromethyl-substituents.
Workup
- washThe reaction mixture was washed once with 1 M aqueous hydrogen solution and twice with distilled water
- dry with materialThe organic layer was dried over sodium sulfate
- concentrationconcentrated in vacuo
- additiona mixture of bromomethyl- and chloromethyl-substituents
Sources & evidence
- ORD record
- ord-e00df9eb5ac44192ad6b97ae406f38f9
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09265763B2
Reaction notes
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