Ethanol → HCID 67195790, compound

HRID 1841949Notes

Reaction equation

HRID 1841949 reaction equation
[CH2:1]([NH:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([S:17]([C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[Cl-].[NH4+]>[Fe].O>[CH2:1]([NH:8][C:9]([N:11]1[CH2:12][CH2:13][N:14]([S:17]([C:20]2[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=2)(=[O:19])=[O:18])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 27533560HCID 27533560, compound

Product 1

HCID 67195790HCID 67195790, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

4-(4-Nitro-benzenesulfonyl)-piperazine-1-carboxylic acid benzylamide (0.5 g, 1.2 mmol) was suspended in a 5:1 mixture of ethanol and water (30 ml). To this solution was added iron powder (0.18 g, 3.1 mmol) followed by saturated ammonium chloride solution (1 ml) and the mixture was heated to 80° C. for three hours. After this time, the reaction mixture was cooled to room temperature and filtered through a pad of celite, the celite was washed with ethanol (10 ml) and ethyl acetate (50 ml) and the solution was concentrated under vacuum. The resulting residue was partitioned between DCM (50 ml) and water (20 ml), the organic layer was separated, dried with MgSO4, filtered and concentrated to afford the title compound (0.47 g, 100% yield) as a colourless oil. Tr=1.60 min, m/z (ES+) (M+H)+ 375.

Workup

  1. temperatureAfter this time, the reaction mixture was cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washthe celite was washed with ethanol (10 ml) and ethyl acetate (50 ml)
  4. concentrationthe solution was concentrated under vacuum
  5. customThe resulting residue was partitioned between DCM (50 ml) and water (20 ml)
  6. customthe organic layer was separated
  7. dry with materialdried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fb483945e88946dca9e4bc5e0a099ffb
Source dataset
uspto-grants-2015_02
Patent number
US08946197B2

Reaction notes

Loading…