Potassium Carbonate → Diisopropyl(((2-((2-methoxyphenyl)carbamoyl)-3-((4-nitro-phenyl)thio)phenyl)amino)methyl)phosphonate

HRID 1476710

Reaction equation

HRID 1476710 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH:35]([O:38][P:39]([CH2:45]Br)(=[O:44])[O:40][CH:41]([CH3:43])[CH3:42])([CH3:37])[CH3:36]>CC#N>[CH:41]([O:40][P:39]([CH2:45][NH:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([S:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[C:3]=1[C:4](=[O:5])[NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])(=[O:44])[O:38][CH:35]([CH3:37])[CH3:36])([CH3:43])[CH3:42]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4366885Diisopropyl bromomethylphosphonateHCID 718115872-amino-N-(2-methoxyphenyl)-6-(4-nitrophenyl-thio)benzamide

Product 1

HCID 71811718Diisopropyl(((2-((2-methoxyphenyl)carbamoyl)-3-((4-nitro-phenyl)thio)phenyl)amino)methyl)phosphonateYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Compound 25 (1.0 equiv.) was dissolved in MeCN (40 mL) and treated with anhydrous potassium carbonate (2.0 equiv.) at room temperature. To this mixture diisopropyl(bromomethyl)phosphonate (1.2 equiv.) was added via a micro syringe. After being stirred for 4 Hours at 60° C., the reaction mixture was concentrated under reduced pressure. The crude residue was diluted by ethyl acetate (50 mL), and washed with water (2×10 mL). Then it was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether) to provide a yellow solid (235.2 mg, 41% yield).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionThe crude residue was diluted by ethyl acetate (50 mL)
  3. washwashed with water (2×10 mL)
  4. dry with materialThen it was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (1:4 v/v ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-88db3d8f35ff41cca758454c7100483a
Source dataset
uspto-grants-2016_08
Patent number
US09402819B2

Linked notes

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