Ammonia → HCID 19605550, compound

HRID 1603557Notes

Reaction equation

HRID 1603557 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[C:4](Br)[N:3]=1.[NH3:19]>O1CCOCC1.CO>[NH2:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([C:6]2[CH:7]=[C:2]([Br:1])[N:3]=[C:4]([NH2:19])[CH:5]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 110146744-(2,6-dibromopyridin-4-yl)sulfonylaniline

Product 1

HCID 19605550HCID 19605550, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

0.196 g (0.0005 mol) of 4-(2,6-dibromopyridine-4-sulphonyl)-phenylamine was dissolved in 10 ml of dioxane, treated with 1.0 ml of sat. NH3 in methanol and stirred in an autoclave at 130° C. for 72 hrs. After removal of the solvent the residue was taken up in ethyl acetate, washed with sat. NH4Cl solution, water and sat. sodium chloride solution, dried over MgSO4 and the solvent was removed. The residue was chromatographed on silica gel with ethyl acetate/hexane 1:2 and 1:1. There was obtained 0.117 g (71%) of 4-(4-aminobenzenesulphonyl)-6-bromopyridin-2-ylamine as a yellowish, amorphous solid; m.p.: 204-205° C.

Workup

  1. customAfter removal of the solvent the residue
  2. washwashed with sat. NH4Cl solution, water and sat. sodium chloride solution
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed
  5. customThe residue was chromatographed on silica gel with ethyl acetate/hexane 1:2 and 1:1

Sources & evidence

ORD record
ord-555af35eae8e4ddbbb0ae52cc93a1557
Source dataset
uspto-grants-1999_11
Patent number
US05990105

Reaction notes

Loading…