Ammonia → Methyl 2-(3-sulfamoylphenyl)acetate

HRID 2211981Notes

Reaction equation

HRID 2211981 reaction equation
[NH3:1].Cl[S:3]([C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4].ClCCl>C(#N)C>[NH2:1][S:3]([C:6]1[CH:7]=[C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])[CH:9]=[CH:10][CH:11]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6344DichloromethaneHCID 23388821Methyl [3-(chlorosulfonyl)phenyl]acetate

Product 1

HCID 85817175Methyl 2-(3-sulfamoylphenyl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
22 °C

Procedure

0.880 Ammonia (0.027 ml) was added to a stirred solution of methyl [3-(chlorosulfonyl)phenyl]acetate (0.35 g) in a 1:1 mixture of dichloromethane and acetonitrile (1.75 ml), and the mixture was stirred at 22° C. for 2 h. The mixture was allowed to stand for a further 18 h, and the solvent was evaporated in vacuo. The residue was re-dissolved in dichloromethane and applied to a silica gel cartridge (10 g Varian Bond Elut, pre-conditioned with dichloromethane). The cartridge was eluted with dichloromethane, chloroform, ether, ethyl acetate, acetone, acetonitrile and methanol (1 column volume each), the fractions containing the product evaporated in vacuo, and the residue passed down a 5 g silica gel cartridge which was prepared and eluted in an identical manner. The product containing fractions were evaporated in vacuo to give a residue which was further purified using mass-directed preparative HPLC, to give the title compound as a colourless gum (0.018 g).

Workup

  1. waitto stand for a further 18 h
  2. customthe solvent was evaporated in vacuo
  3. dissolutionThe residue was re-dissolved in dichloromethane
  4. washThe cartridge was eluted with dichloromethane, chloroform, ether, ethyl acetate, acetone, acetonitrile and methanol (1 column volume each), the fractions
  5. additioncontaining the product
  6. customevaporated in vacuo
  7. customwas prepared
  8. washeluted in an identical manner
  9. additionThe product containing fractions
  10. customwere evaporated in vacuo
  11. customto give a residue which
  12. customwas further purified

Sources & evidence

ORD record
ord-7b5ac40a1df24297b1ac4733005a18e2
Source dataset
uspto-grants-2006_09
Patent number
US07101882B2

Reaction notes

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