Ammonia → HCID 59191210, compound

HRID 626052Notes

Reaction equation

HRID 626052 reaction equation
[NH3:1].[CH2:2]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][C:10]=2[F:19])=[C:6]([O:22][CH3:23])[CH:5]=1)[CH3:3]>C1COCC1.C(OCC)(=O)C>[CH2:2]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([S:15]([NH2:1])(=[O:17])=[O:16])=[CH:11][C:10]=2[F:19])=[C:6]([O:22][CH3:23])[CH:5]=1)[CH3:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 59191302HCID 59191302, compound

Product 1

HCID 59191210HCID 59191210, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Conc. NH3 (5.0 mmol; 0.28 mL) was slowly added to a solution of 4-(4-ethyl-2-methoxyphenoxy)-3-fluorobenzenesulfonyl chloride (1.0 mmol; 344 mg) in THF (5 mL), under argon at 0° C. The reaction was stirred overnight with slow warming to room temperature. Diluted with ethyl acetate (5 mL), the mixture was washed with HCl (1N), and sat. NH4Cl. The organic phase was dried over MgSO4, concentrated. The residue was purified by chromatography (dichloromethane/ethyl acetate gradient) to yield the title compound as an off-white solid (108 mg; 0.33 mmol; 33%).

Workup

  1. washthe mixture was washed with HCl (1N), and sat. NH4Cl
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography (dichloromethane/ethyl acetate gradient)

Sources & evidence

ORD record
ord-d1af689120554c1fabc22c5d8c01adc1
Source dataset
uspto-grants-2016_04
Patent number
US09309179B2

Reaction notes

Loading…