HCID 54480594, compound → HCID 19353526, compound

HRID 378312Notes

Reaction equation

HRID 378312 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)C)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[C:4]([C:22]([F:25])([F:24])[F:23])[N:3]=1>[OH-].[Na+].O1CCOCC1>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]2[CH:5]=[C:4]([C:22]([F:24])([F:25])[F:23])[N:3]=[C:2]([Cl:1])[CH:7]=2)(=[O:10])=[O:11])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 54480594HCID 54480594, compound

Product 1

HCID 19353526HCID 19353526, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

0.20 g (0.0005 mol) of N-[4-(2-chloro-6-trifluoromethyl-pyridin-4-ylsulfamoyl)-phenyl]-acetamide was dissolved in a mixture of 5 ml of 1N NaOH and 5 ml of dioxan and boiled at reflux for 5 hours. After cooling the dioxan was distilled off, the residue was adjusted to pH 6 with 0.1N HCl, the aqueous phase was extracted with ethyl acetate, back-washed with saturated sodium chloride solution and the organic phase was dried over Na2SO4. Subsequently, chromatography was carried out on silica gel with ethyl acetate/hexane 1:4. There was obtained 0.06 g (34%) of 4-amino-N-(2-chloro-6-trifluoromethyl-pyridin-4-yl)-benzenesulfonamide as pale yellow crystals; m.p.: 179-181° C.

Workup

  1. temperatureat reflux for 5 hours
  2. distillationwas distilled off
  3. extractionthe aqueous phase was extracted with ethyl acetate
  4. washback-washed with saturated sodium chloride solution
  5. dry with materialthe organic phase was dried over Na2SO4

Sources & evidence

ORD record
ord-a780918d9e9a48c68830cc8d242d11b4
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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