Triethylamine → N-(2-(dimethylamino)ethyl)-2-methylbenzo[d]thiazole-6 sulfonamide
Reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([S:11](Cl)(=[O:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(N(CC)CC)C.[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH2:26]>C1COCC1>[CH3:22][N:23]([CH3:27])[CH2:24][CH2:25][NH:26][S:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([CH3:1])[S:3][C:4]=2[CH:10]=1)(=[O:13])=[O:12]Participants
Procedure
To a solution of Compound 8 (7.0 g, 28.26 mmol) in THF (70 mL), a mixture of triethylamine (7.9 mL, 56.52 mmol) and N,N-dimethylethylene-diamine (4.67 mL, 42.38 mmol) in 20 mL THF was added dropwise. The combined mixture was stirred at room temperature for 2 hours during which time TLC showed complete disappearance of Compound 8. Solvents were removed in the rotary evaporator and the residue thus obtained was partitioned between chloroform (100 mL) and water (100 mL). The organic layer was washed with water (2×100 mL), brine (1×100 mL), dried (sodium sulfate) and evaporated to provide Compound 9 as a sticky oily solid (7.1 g, 84% yield). It was used further in the synthesis without any purification. The structure of Compound 9 is given below:
Workup
- additionwas added dropwise
- customSolvents were removed in the rotary evaporator
- customthe residue thus obtained
- customwas partitioned between chloroform (100 mL) and water (100 mL)
- washThe organic layer was washed with water (2×100 mL), brine (1×100 mL)
- dry with materialdried (sodium sulfate)
- customevaporated
Sources & evidence
- ORD record
- ord-f5b58df3379f4aef8a85968a9ce93cdd
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604204B2
Reaction notes
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