Dimethylformamide → HCID 73704949, compound

HRID 24624Notes

Reaction equation

HRID 24624 reaction equation
C([C:4]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)=[CH:5][C:6]([NH:8][CH2:9][CH:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7])(=O)C.S(O)(O)(=O)=O.C[NH:31][C:32](=[NH:34])[SH:33].[C:35]([O-])(=O)[CH3:36].[Na+].[CH3:40]N(C=O)C>>[C:12]1([CH:11]=[CH:10][CH2:9][NH:8][C:6]([C:5]2[CH:4]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[N:34]=[C:32]([S:33][CH3:40])[NH:31][C:35]=2[CH3:36])=[O:7])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 697480813-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamideHCID 178485225HCID 178485225, compound

Product 1

HCID 73704949HCID 73704949, compound

Conditions

Temperature
120 °C

Procedure

120 mg (0.353 mmol) of 3-acetyl-3-(3-chlorophenyl)-N-(3-phenyl-2-propene-1-yl)acrylamide was dissolved in 10 ml of DMF. 78.6 mg (0.283 mmol) of methylisothiourea monosulfate and 34.7 mg (0.424 mmol) of sodium acetate were added to the obtained solution at room temperature, and they were stirred at that temperature overnight. DMF was evaporated under reduced pressure. The residue was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. 2-propanol was added to the residue, and they were heated to 120° C. and stirred overnight. The residue was purified by the silica gel chromatography (hexane/ethyl acetate=5/1) to obtain the title compound.

Workup

  1. customDMF was evaporated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. addition2-propanol was added to the residue, and they
  7. stirringstirred overnight
  8. customThe residue was purified by the silica gel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-c666f253a839400a8a7ff58395fd6c92
Source dataset
uspto-grants-2005_02
Patent number
US06855716B2

Reaction notes

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