Water → HCID 59446492, compound

HRID 1807428Notes

Reaction equation

HRID 1807428 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(=O)([O-])[O-].[K+].[K+].FC(F)(F)S(O[CH2:34][P:35]([O:40][CH2:41][CH3:42])([O:37][CH2:38][CH3:39])=[O:36])(=O)=O.O>CN(C)C=O.C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[C:4]([S:9]([N:12]([CH2:34][P:35](=[O:36])([O:40][CH2:41][CH3:42])[O:37][CH2:38][CH3:39])[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)(=[O:11])=[O:10])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 11833487(Diethoxyphosphoryl)methyl trifluoromethanesulfonateHCID 25044530HCID 25044530, compound

Product 1

HCID 59446492HCID 59446492, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.56 g 3,5-dichloro-N-(1H-indol-5-yl)-phenylsulphonamide are dissolved in 25 ml dimethylformamide. To this, 3.11 g potassium carbonate and 2.93 ml diethoxy-phosphorylmethyl trifluoro-methanesulphonate are added dropwise. The mixture is stirred overnight at ambient temperature, divided between water and ethyl acetate and the aqueous phase is extracted twice with ethyl acetate. The combined organic phases are washed twice with water and once with saturated sodium chloride solution and dried on magnesium sulphate. The solvents are eliminated in vacuo, the residue is dissolved in hot ethyl acetate and after cooling to ambient temperature the precipitated solid is suction filtered. Further product is obtained by freeing the mother liquor in vacuo from the volatile constituents and chromatographing the residue on silica gel (cyclohexane/ethyl acetate 50:50 to 25:75).

Workup

  1. extractionthe aqueous phase is extracted twice with ethyl acetate
  2. washThe combined organic phases are washed twice with water and once with saturated sodium chloride solution
  3. customdried on magnesium sulphate
  4. dissolutionthe residue is dissolved in hot ethyl acetate
  5. temperatureafter cooling to ambient temperature the precipitated solid
  6. filtrationfiltered
  7. customFurther product is obtained

Sources & evidence

ORD record
ord-a0f9c7f33b324889b78852d70eaffb2c
Source dataset
uspto-grants-2013_01
Patent number
US08357689B2

Reaction notes

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