Methane → 3-(5-Chloro-2-methoxybenzamido)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman

HRID 1457747Notes

Reaction equation

HRID 1457747 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([CH:26]=1)[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:24][CH3:25])=[C:16]([S:20](=[O:23])(=[O:22])[NH2:21])[CH:17]=2)[O:12][CH2:11]1)=[O:8].[OH-].[Na+].[CH3:31][NH:32][C:33](=[O:38])C(Cl)(Cl)Cl.C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:27][CH3:28])=[C:6]([CH:26]=1)[C:7]([NH:9][CH:10]1[CH2:19][C:18]2[C:13](=[CH:14][C:15]([O:24][CH3:25])=[C:16]([S:20]([NH:21][C:33]([NH:32][CH3:31])=[O:38])(=[O:22])=[O:23])[CH:17]=2)[O:12][CH2:11]1)=[O:8]

Participants

6

Reactant 4

HCID 297MethaneHCID 14798Sodium HydroxideHCID 2486522,2,2-Trichloro-n-methylacetamideHCID 221004303-(5-Chloro-2-methoxybenzamido)-6-sulfamoyl-7-methoxychroman

Product 1

HCID 98914753-(5-Chloro-2-methoxybenzamido)-6-(methylaminocarbonylaminosulfonyl)-7-methoxychroman

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.71 g (4 mmol) of 3-(5-chloro-2-methoxybenzamido)-6-sulfamoyl-7-methoxychroman were heated at 80° C. for 30 minutes in 10 ml of dry DMSO after addition of 0.4 g (10 mmol) of freshly powdered sodium hydroxide and 1.05 g (6 mmol) of N-methyltrichloroacetamide. The cooled reaction mixture was introduced into ice-water, clarified with active charcoal and acidified to pH 1. The precipitate was filtered off with suction, dried and recrystallized twice from ethanol. The product had a melting point of 256°-257° C.

Workup

  1. customThe cooled reaction mixture
  2. filtrationThe precipitate was filtered off with suction
  3. customdried
  4. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-2a55610dab5f483c8a7bf04c3eed9c7e
Source dataset
uspto-grants-1998_12
Patent number
US05849755

Reaction notes

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