Hydrochloric Acid → HCID 3636917, compound

HRID 1049027Notes

Reaction equation

HRID 1049027 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.N1C=CC=CC=1.[CH2:19]([NH2:23])[CH:20]([CH3:22])[CH3:21].Cl>C(Cl)Cl>[CH2:19]([NH:23][S:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6558IsobutylamineHCID 74014-Methoxybenzenesulfonyl chloride

Product 1

HCID 3636917HCID 3636917, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxybenzenesulfonylchloride (1 g, 4.8 mmol) in DCM (20 mL) was added pyridine (1.17 mL, 14.5 mmol) followed by isobutylamine (961 μL, 9.7 mmol) and the reaction was stirred at room temperature for 16 hours. 1 M aqueous HCl was added, extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (100% DCM) to give N-isobutyl-4-methoxy-benzenesulfonamide (1.03 g, 88%). LCMS (m/z, Method A) ES− 242 [M−1]−.

Workup

  1. extractionextracted with DCM
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated
  4. customthen purified by silica gel column chromatography (100% DCM)

Sources & evidence

ORD record
ord-9012a9e6d3534fd3a4beab3d6ab31f29
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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