Water → HCID 86721878, compound

HRID 1049028Notes

Reaction equation

HRID 1049028 reaction equation
[CH2:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[H-].[Na+].[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1.O>CC(N(C)C)=O>[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[S:6]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)(=[O:8])=[O:7])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 3636917HCID 3636917, compound

Product 1

HCID 86721878HCID 86721878, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of N-isobutyl-4-methoxy-benzenesulfonamide (1.03 g, 4.2 mmol) in anhydrous dimethylacetamide (20 mL) at 0° C. was added NaH (60% dispersion in mineral oil, 186 mg, 4.6 mmol) until no more gas evolved then stirred for a further 10 minutes. 4-Chlorobenzylbromide (951 mg, 4.6 mmol) was added and the reaction heated at 90° C. for 2 hours. The reaction was left to cool to room temperature, water was added, extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-50% DCM in cyclohexane) to give N-(4-chloro-benzyl)-N-isobutyl-4-methoxy-benzenesulfonamide (1.03 g, 67%). LCMS (m/z, Method A)) ES+ 368 [M+1]+.

Workup

  1. waitThe reaction was left
  2. temperatureto cool to room temperature
  3. extractionextracted with DCM
  4. filtrationfiltered through a phase separator
  5. concentrationconcentrated
  6. customthen purified by silica gel column chromatography (0-50% DCM in cyclohexane)

Sources & evidence

ORD record
ord-94a5eac7f08c4e67b07ba50c58e5f45c
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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