Sodium hydride → N-((4-Chloro-2,6-diisopropylphenyl)carbamoyl)-3-(2-hydroxypropan-2-yl)benzenesulfonamide

HRID 2303598Notes

Reaction equation

HRID 2303598 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]([OH:14])([CH3:13])[CH3:12])[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[H-].[Na+].[H][H].[Cl:19][C:20]1[CH:25]=[C:24]([CH:26]([CH3:28])[CH3:27])[C:23]([N:29]=[C:30]=[O:31])=[C:22]([CH:32]([CH3:34])[CH3:33])[CH:21]=1>O1CCCC1>[Cl:19][C:20]1[CH:21]=[C:22]([CH:32]([CH3:34])[CH3:33])[C:23]([NH:29][C:30]([NH:1][S:2]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([OH:14])([CH3:12])[CH3:13])[CH:6]=2)(=[O:3])=[O:4])=[O:31])=[C:24]([CH:26]([CH3:28])[CH3:27])[CH:25]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 154799593-(2-Hydroxypropan-2-yl)benzenesulfonamideHCID 154799605-Chloro-2-isocyanato-1,3-di(propan-2-yl)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 9911728N-((4-Chloro-2,6-diisopropylphenyl)carbamoyl)-3-(2-hydroxypropan-2-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(3-aminosulfonylphenyl)-propan-2-ol (26.5 grams) in tetrahydrofuran was added sodium hydride (5.2 grams of a 60% dispersion in mineral oil) in several portions. Once hydrogen evolution had subsided, 4-chloro-2,6-diisopropylphenylisocyanate (30.8 grams) was added in one portion, and the resulting mixture was heated to reflux for twelve hours. The mixture was then cooled to room temperature and concentrated in vacuo. The resulting foam was dissolved in water, made basic with 1N sodium hydroxide and extracted with two portions of a 1:1 ration of ether/hexane. The aqueous layer was acidified with 1N hydrochloric acid, and the resulting white solid was filtered, washed with water and dried. This afforded 50 grams of a white solid which was recrystallized from wet ethyl acetate/hexane afforded the title compound, melting point 160.5-162.0° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for twelve hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resulting foam was dissolved in water
  5. extractionextracted with two portions of a 1:1 ration of ether/hexane
  6. filtrationthe resulting white solid was filtered
  7. washwashed with water
  8. customdried
  9. customThis afforded 50 grams of a white solid which was recrystallized from wet ethyl acetate/hexane

Sources & evidence

ORD record
ord-a7469359f5024110885a7a7ebc890284
Source dataset
uspto-grants-2002_08
Patent number
US06433009B1

Reaction notes

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