Ethyl Acetate → HCID 59446514, compound

HRID 1510320Notes

Reaction equation

HRID 1510320 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([N:12]([CH2:22][P:23](=[O:30])([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])[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:31](OCC)(=[O:33])[CH3:32].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[C:31]([N:18]1[C:19]2[C:15](=[CH:14][C:13]([N:12]([CH2:22][P:23](=[O:30])([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[S:9]([C:4]3[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=3)(=[O:10])=[O:11])=[CH:21][CH:20]=2)[CH:16]=[CH:17]1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59446492HCID 59446492, compound

Product 1

HCID 59446514HCID 59446514, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

100 mg diethyl {[(3,5-dichloro-phenylsulphonyl)-(1H-indol-5-yl)-amino]-methyl}-phosphonate are dissolved in 1 ml acetic anhydride and refluxed overnight. After cooling to ambient temperature the mixture is divided between ethyl acetate and ice water. Then it is neutralised by the addition of saturated sodium hydrogen carbonate solution. The phases are separated and the organic phase is washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution. After drying with magnesium sulphate the solvents are eliminated in vacuo and the residue is chromatographed on silica gel (petroleum ether/ethyl acetate 1:2 to 1:3).

Workup

  1. temperaturerefluxed overnight
  2. customThe phases are separated
  3. washthe organic phase is washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  4. dry with materialAfter drying with magnesium sulphate the solvents
  5. customthe residue is chromatographed on silica gel (petroleum ether/ethyl acetate 1:2 to 1:3)

Sources & evidence

ORD record
ord-b6bb1c69f4924fb5b4bc2a4de6dde0d8
Source dataset
uspto-grants-2012_07
Patent number
US08211923B2

Reaction notes

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