2-Methylbenzenesulfonamide → HCID 9825050, compound

HRID 2081708Notes

Reaction equation

HRID 2081708 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17](O)=[O:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([O-:3])=[O:2].[CH3:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[S:30]([NH2:33])(=[O:32])=[O:31].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([NH:33][S:30]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH3:23])(=[O:31])=[O:32])=[O:18])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 69242-MethylbenzenesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 19780392HCID 19780392, compound

Product 1

HCID 9825050HCID 9825050, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of the carboxylic acid (Example 33) (0.5 g), 2-methylbenzene sulphonamide (0.28 g), 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (0.37 g) and 4-dimethylaminopyridine (0.05 g) in dichloromethane (6 ml) was stirred at room temperature for 72 hours. The reaction mixture was diluted with dichloromethane and washed with water and brine. The organic phase was dried over anhydrous magnesium sulphate, filtered and evaporated in vacuo. Purification by flash chromatography on silica, eluting with 0-2% ethyl acetate in dichloromethane, gave a yellow oil which, on crystallisation from methanol, afforded N-[1-(3-nitrobenzyl)indolin-5-ylcarbonyl]-2-methylbenzene sulphonamide, m.p. 159°-163° C.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customPurification by flash chromatography on silica
  6. washeluting with 0-2% ethyl acetate in dichloromethane
  7. customgave a yellow oil which
  8. customon crystallisation from methanol

Sources & evidence

ORD record
ord-7bbda33eddac4d6898b8d21521697d91
Source dataset
uspto-grants-1993_02
Patent number
US05185361

Reaction notes

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