Methanesulfonyl chloride → 2-[N-(4-Methanesulphonamidobenzyl)-N-methylamino]-5-methanesulphonamidoindane
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([N:16]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)[CH3:17])[CH2:10]2>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH3:1][S:2]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH:11]([N:16]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:23][CH:24]=1)[CH3:17])[CH2:10]2)(=[O:4])=[O:3]Participants
Procedure
Methanesulphonyl chloride (0.53 ml) was added to 5-amino-2-[N-(4-aminobenzyl)-N-methylamino]indane (1.1 g) in pyridine and the reaction mixture was stirred at room temperature for 17 hours. The solvent was then removed by evaporation in vacuo and the residue taken up in methylene chloride, washed with aqueous sodium bicarbonate, dried (MgSO4) and evaporated in vacuo. The resulting gum was purified by column chromatography on silica eluting with methylene chloride containing methanol (0% up to 2%). The product-containing fractions were combined and evaporated to dryness in vacuo to give a colourless foam. This foam was dissolved in chloroform and the solution was evaporated to dryness in vacuo to give the title compound as a colourless foam, yield 0.2 g.
Workup
- customThe solvent was then removed by evaporation in vacuo
- washwashed with aqueous sodium bicarbonate
- dry with materialdried (MgSO4)
- customevaporated in vacuo
- customThe resulting gum was purified by column chromatography on silica eluting with methylene chloride
- additioncontaining methanol (0% up to 2%)
- customevaporated to dryness in vacuo
- customto give a colourless foam
- customthe solution was evaporated to dryness in vacuo
Sources & evidence
- ORD record
- ord-9652492b00294be1a172c2e304feac5b
- Source dataset
- uspto-grants-1989_05
- Patent number
- US04829071
Reaction notes
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