Ammonium Hydroxide → HCID 57562895, compound

HRID 1770818Notes

Reaction equation

HRID 1770818 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[C:9]([CH3:12])[C:10]=1[F:11])(=[O:4])=[O:3].[OH-].[NH4+:17]>C(OCC)(=O)C>[NH2:17][S:2]([C:5]1[CH:6]=[C:7]([N+:13]([O-:15])=[O:14])[CH:8]=[C:9]([CH3:12])[C:10]=1[F:11])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 575628801187082-98-9

Product 1

HCID 57562895HCID 57562895, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The resulting oily residue of compound 26 was taken up in ethyl acetate (100 mL) and stirred with ammonium hydroxide (100 mL, 30% aqueous solution) overnight at room temperature. After the ethyl acetate layer was separated, the aqueous layer was extracted with ethyl acetate (2×50 mL). The organic layers were combined, dried over anhydrous sodium sulfate and the solvent was removed under vacuum. The dark oily residue was chromatographed (silica gel, hexanes then 10%, 20%, up to 50% ethyl acetate in hexanes to afford 3-aminosulfonyl-4-fluoro-5-methylnitrobenzene (27). LCMS: purity: 89%; MS (m/z): 235 (MH+).

Workup

  1. customAfter the ethyl acetate layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under vacuum
  5. customThe dark oily residue was chromatographed (silica gel, hexanes

Sources & evidence

ORD record
ord-a947b3a8037b460fb90d9207dd6c8976
Source dataset
uspto-grants-2016_02
Patent number
US09248190B2

Reaction notes

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