Ethanol → HCID 86676778, compound

HRID 2411483Notes

Reaction equation

HRID 2411483 reaction equation
[Cl-].[NH4+].C(O)C.[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:19][CH2:18][N:17]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH2:32][CH2:31][CH2:30][S:29]3(=[O:34])=[O:33])=[CH:24][C:23]=2[N+:35]([O-])=O)=[O:21])[CH2:16][CH2:15]1>[Fe].O>[NH2:35][C:23]1[CH:24]=[C:25]([N:28]2[CH2:32][CH2:31][CH2:30][S:29]2(=[O:34])=[O:33])[CH:26]=[CH:27][C:22]=1[C:20]([N:17]1[CH2:18][CH2:19][N:14]([C:8]2[CH:9]=[CH:10][C:11]([CH3:13])=[CH:12][C:7]=2[CH3:6])[CH2:15][CH2:16]1)=[O:21]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 71252579HCID 71252579, compound

Product 1

HCID 86676778HCID 86676778, compoundYield 52.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Ammonium chloride (504 mg) and iron (364 mg) were added to a solution of ethanol (9 mL) and water (2.3 mL), [4-(2,4-dimethylphenyl)piperazin-1-yl][4-(1,1-dioxo-1λ6-isothiazolidin-2-yl)-2-nitrophenyl]methanone (770 mg) described in Example 100 was added while stirring at 60° C.-70° C. After completion of the reaction, the insoluble material was collected by filtration, and the filtrate was concentrated. To the obtained residue was added aqueous sodium hydrogen carbonate solution, the mixture was extracted with ethyl acetate, and the solvent was evaporated. The obtained residue was purified by column chromatography (chloroform:methanol) to give the title compound (380 mg).

Workup

  1. additionwas added
  2. customAfter completion of the reaction
  3. filtrationthe insoluble material was collected by filtration
  4. concentrationthe filtrate was concentrated
  5. additionTo the obtained residue was added aqueous sodium hydrogen carbonate solution
  6. extractionthe mixture was extracted with ethyl acetate
  7. customthe solvent was evaporated
  8. customThe obtained residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-84256986a0414c8ab33a303770fff2b1
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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