Toluene → N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamide

HRID 971081Notes

Reaction equation

HRID 971081 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].Cl.[CH2:7]([C:11]1[O:12][C:13]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][C:14]=2[CH:15]=1)[CH2:8][CH2:9][CH3:10].C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl-].C[N+](C)(C)C.O>[CH2:7]([C:11]1[O:12][C:13]2[CH:19]=[CH:18][C:17]([NH:20][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:16][C:14]=2[CH:15]=1)[CH2:8][CH2:9][CH3:10]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 98133102-butylbenzofuran-5-amine Hydrochloride

Product 1

HCID 9878493N-(2-Butyl-1-benzofuran-5-yl)methanesulfonamideYield 94.4%

Reagents, catalysts & solvents 2

HCID 6379Tetramethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

Methanesulfonyl chloride (0.92 g, 0.6 mL, 8.0 mmol) was added dropwise to a stirred boiling mixture of 2-butyl-5-benzofuranylamine hydrochloride [12a] (0.90 g, 4.0 mmol), tetramethylammonium chloride (0.11 g, 1.0 mmol) and toluene (10 mL) for 1 hour. The mixture was stirred under reflux conditions for 1 hour. Ethyl acetate (20 mL) and water (30 mL) were added to the cold mixture. The organic layer was separated and aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over sodium sulfate and evaporated under reduced pressure to give 1.01 g (94.0%) of N-(2-butyl-5-benzofuranyl)methanesulfonamide [14] with mp 104.9-105.9° C.

Workup

  1. customThe organic layer was separated
  2. extractionaqueous layer was extracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f07fa64cbf0549c7803843bcaecc4ccb
Source dataset
uspto-grants-2007_12
Patent number
US07312345B2

Reaction notes

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