Ammonium Hydroxide → HCID 66857363, compound

HRID 252259Notes

Reaction equation

HRID 252259 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][C:10]=2[CH3:18])=[CH:5][CH:4]=1.[OH-].[NH4+:20]>CC(C)=O>[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([S:14]([NH2:20])(=[O:16])=[O:15])=[CH:11][C:10]=2[CH3:18])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 866167205-(6-Methoxy-pyridin-3-yl)-4-methyl-thiophene-2-sulfonyl chloride

Product 1

HCID 66857363HCID 66857363, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-(6-Methoxy-pyridin-3-yl)-4-methyl-thiophene-2-sulfonyl chloride (0.19 g, 0.63 mmol) was dissolved in acetone (6 ml) and added dropwise to an aqueous ammonium hydroxide solution (25%, 1.2 ml). After 1 hour the solvent was removed under reduced pressure, the residue diluted with water and extracted with ethyl acetate (3×). The combined organic extracts were washed with water, brine, dried (MgSO4.2H2O), filtered and concentrated under reduced pressure to yield a crude that was purified over silica gel (n-heptane-ethyl acetate 1:2 to 2:1 v/v) to yield a beige solid: 0.12 g (62%), MS: m/e 283.0 (MH−).

Workup

  1. customAfter 1 hour the solvent was removed under reduced pressure
  2. additionthe residue diluted with water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organic extracts were washed with water, brine
  5. dry with materialdried (MgSO4.2H2O)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto yield a crude that
  9. customwas purified over silica gel (n-heptane-ethyl acetate 1:2 to 2:1 v/v)
  10. customto yield a beige solid

Sources & evidence

ORD record
ord-649d919766c54de980b15d73a0e2ca24
Source dataset
uspto-grants-2011_01
Patent number
US07868030B2

Reaction notes

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