1,1'-Carbonyldiimidazole → HCID 67441840, compound

HRID 1665008Notes

Reaction equation

HRID 1665008 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=O)(=[O:4])=[O:3].C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:26]([N:33]([CH2:47][C:48]([NH:50][NH2:51])=[O:49])[S:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]([F:46])([F:45])[F:44])(=[O:36])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C(=O)C.C(OCC)(=O)C>[CH2:26]([N:33]([CH2:47][C:48]([NH:50][NH:51][C:8](=[O:10])[C:7]1[CH:11]=[CH:12][CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=1)=[O:49])[S:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[C:43]([F:44])([F:45])[F:46])(=[O:36])=[O:35])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 2203803-Methanesulfonylbenzoic acidHCID 67440054HCID 67440054, compound

Product 1

HCID 67441840HCID 67441840, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 3-methylsulfonylbenzoic acid (60 mg) in N,N-dimethylacetamide (1.3 mL) was added 1,1′-carbonyl-diimidazole (52 mg). The mixture was stirred at 50° C. for 20 min. After cooling to r.t., N-benzyl-N-hydrazinocarbonylmethyl-2-trifluoromethyl-benzenesulfonamide (100 mg) was added and the mixture was stirred at 100° C. overnight. After cooling to r.t. the mixture was diluted with ethyl acetate and washed with water. The organic phase was dried (MgSO4), filtered and concentrated under reduced pressure. The product was purified by chromatography (SiO2, dichloromethane to dichloromethane/methanol 95:5) to give N-benzyl-N-{2-[N′-(3-methanesulfonyl-benzoyl)-hydrazino]-2-oxo-ethyl}-2-trifluoromethyl-benzenesulfonamide (111 mg) as a colorless oil. MS: 570.3 ([M+H]+)

Workup

  1. temperatureAfter cooling to r.t.
  2. stirringthe mixture was stirred at 100° C. overnight
  3. temperatureAfter cooling to r.t. the mixture
  4. washwashed with water
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by chromatography (SiO2, dichloromethane to dichloromethane/methanol 95:5)

Sources & evidence

ORD record
ord-30adce3d434146e7814d169c75c995b7
Source dataset
uspto-grants-2011_10
Patent number
US08039493B2

Reaction notes

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