Sulfuric Acid → 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulphonamide sulphate

HRID 742378

Reaction equation

[S:1](=[O:5])(=[O:4])([OH:3])[OH:2].[CH3:6][N:7]([CH3:25])[CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][S:20]([NH:23][CH3:24])(=[O:22])=[O:21])[CH:17]=2)[NH:12][CH:11]=1>O.C(O)C>[S:1]([OH:5])([OH:4])(=[O:3])=[O:2].[CH3:25][N:7]([CH3:6])[CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([CH2:19][S:20]([NH:23][CH3:24])(=[O:21])=[O:22])[CH:17]=2)[NH:12][CH:11]=1

Participants

Conditions

Temperature: 450 °C

Procedure

Sulphuric acid solution (2N, 169 ml) was diluted with water (106 ml) and added rapidly dropwise to a stirred solution of 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole -5-methanesulphonamide or (100 g) in ethanol (2.31) and water (25 ml) at reflux. The resulting solution was cooled to 450° C., then seeded, cooled to 40° C. and aged 1 h. The reaction mixture was filtered and the filtrate washed with ethanol (50 ml) then dried at 400° C. in vacuo to give the title compound (114 g) in a solvated form, m.p. 157° C. (decomp.).

Workup

temperaturecooled to 40° C. and aged 1 h
filtrationThe reaction mixture was filtered
washthe filtrate washed with ethanol (50 ml)
customthen dried at 400° C. in vacuo

Sources & evidence

ORD record: ord-6def53f673344b1bb26207b5555d65c4
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05554639

Linked notes

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