Water → HCID 22891648, compound

HRID 1028401Notes

Reaction equation

HRID 1028401 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].[OH-].[NH4+:15].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH3:9])=[CH:4][C:3]=1[S:10]([NH2:15])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 55279357HCID 55279357, compound2×

Product 1

HCID 22891648HCID 22891648, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-chloro-5-ethylbenzenesulfonyl chloride (0.41 g, 1.7 mmol, the product of Step A) in tetrahydrofuran (30 mL) was added 30% ammonium hydroxide (0.41 mL, 3.5 mmol) dropwise. The reaction mixture was stirred for 15 minutes, during which time a suspension formed. To this mixture water (10 mL) was added, and the tetrahydrofuran was evaporated under reduced pressure to precipitate a solid. The solid was dissolved in diethyl ether, dried over magnesium sulfate, and concentrated under reduced pressure. Diethyl ether and hexane were added to precipitate a solid. The solid was isolated by filtration to afford 190 mg of the title compound. 1H NMR (CDCl3) δ 7.95 (s, 1H), 7.43 (d, 1H), 7.35 (d, 1H), 5.08 (br s, 2H), 2.71 (q, 2H), 1.25 (t, 3H).

Workup

  1. customformed
  2. customthe tetrahydrofuran was evaporated under reduced pressure
  3. customto precipitate a solid
  4. dissolutionThe solid was dissolved in diethyl ether
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionDiethyl ether and hexane were added
  8. customto precipitate a solid
  9. customThe solid was isolated by filtration

Sources & evidence

ORD record
ord-451547a456a74aecbb0ad6adaa58e2b1
Source dataset
uspto-grants-2014_05
Patent number
US08735588B2

Reaction notes

Loading…