HCID 11183896, compound → HCID 961798, compound

HRID 379719Notes

Reaction equation

HRID 379719 reaction equation
C(NCCO[C:8]1[C:14]([CH3:15])=[CH:13][C:11]([NH2:12])=[CH:10][C:9]=1[CH3:16])(C)C.[CH3:17][S:18]([NH:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25])(=[O:20])=[O:19]>>[CH3:17][S:18]([NH:21][C:22]1[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=1[C:24]([NH:12][C:11]1[CH:10]=[C:9]([CH3:16])[CH:8]=[C:14]([CH3:15])[CH:13]=1)=[O:25])(=[O:20])=[O:19]

Participants

3

Reactant 2

HCID 11183896HCID 11183896, compoundHCID 18368270HCID 18368270, compound

Product 1

HCID 961798HCID 961798, compoundYield 57.7%

Procedure

4-[2-(Isopropylamino)ethoxy]3,5-dimethylaniline (2.6 g) solution in dimethylformamido (15 ml) was added with 2-(methanesulfonamido)benzoyl chloride (3.0 g) and the mixture was stirred for 2 hours at room temperature. After being concentrated under vacuum, the reaction mixture was dissolved into chloroform (50 ml) and extracted with 1N sodium hydroxide (100 ml). Resultant aqueous layer was neutralized with 1N HCl (100 ml) and extracted with chloroform (150 ml). Chloroform layer obtained was concentrated and purified by silica-gel column chromatography (chloroform:methanol=10:1) to obtain 4′-[2-isopropylamino) ethoxy]-2-methanesulfonamido-3′,5′-dimethylbenzanilide (2.15 g) as white solid.

Workup

  1. concentrationAfter being concentrated under vacuum
  2. dissolutionthe reaction mixture was dissolved into chloroform (50 ml)
  3. extractionextracted with 1N sodium hydroxide (100 ml)
  4. extractionextracted with chloroform (150 ml)
  5. customChloroform layer obtained
  6. concentrationwas concentrated
  7. custompurified by silica-gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-9bb57287ddf243f98b44496781bfc4da
Source dataset
uspto-grants-2001_10
Patent number
US06300368B1

Reaction notes

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