Water → N-{4-(2-{4-[(aminocarbonothioyl)amino]phenyl}ethyl)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide

HRID 2117911Notes

Reaction equation

HRID 2117911 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:26][C:27](=[O:29])[CH3:28])[S:13][C:14]=2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:4][CH:3]=1.C([N:38]=[C:39]=[S:40])(=O)C1C=CC=CC=1.O>CC(C)=O>[NH2:38][C:39]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]([NH:26][C:27](=[O:29])[CH3:28])[S:13][C:14]=2[CH2:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)=[CH:6][CH:7]=1)=[S:40]

Participants

5

Reactant 3

HCID 962WaterHCID 68284Benzoyl isothiocyanateHCID 21914845N-(4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl)acetamide

Product 1

HCID 21914747N-{4-(2-{4-[(aminocarbonothioyl)amino]phenyl}ethyl)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamideYield 103.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a ice-cold solution of N-{4-[2-(4-aminophenyl)ethyl]-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (247.6 mg) in acetone (4.8 ml) was added benzoyl isothiocyanate (94.1 mg), and the mixture was stirred at r.t. for 1 hour. Water was added to the mixture, and the mixture was extracted with AcOEt. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residual amorphous substance was dissolved in EtOH (5 ml), and 6N—NaOH (0.288 ml) was added to the solution at 0° C. The reaction mixture was stirred at r.t. for 2 hours, and neutralized with 1N—HCl at 0° C. The mixture was extracted with AcOEt. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was solidified with ethyl ether to give N-{4-(2-{4-[(aminocarbonothioyl)amino]phenyl}ethyl)-5-[4-(methylsulfonyl)benzyl]-1,3-thiazol-2-yl}acetamide (290.7 mg) as an off-white solid.

Workup

  1. extractionthe mixture was extracted with AcOEt
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residual amorphous substance was dissolved in EtOH (5 ml)
  6. addition6N—NaOH (0.288 ml) was added to the solution at 0° C
  7. stirringThe reaction mixture was stirred at r.t. for 2 hours
  8. customneutralized with 1N—HCl at 0° C
  9. extractionThe mixture was extracted with AcOEt
  10. washThe organic layer was washed with water and brine
  11. dry with materialdried over anhydrous MgSO4
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0f5b7567643b4051a0f7d4c28f440a66
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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