Triethylamine → N-butyl-N-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)methanesulfonamide

HRID 850022Notes

Reaction equation

HRID 850022 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([NH:10][CH:11]1[CH2:15][S:14](=[O:17])(=[O:16])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]1=2)[CH2:7][CH2:8][CH3:9].C(N(CC)CC)C>C1COCC1>[CH2:6]([N:10]([CH:11]1[CH2:15][S:14](=[O:17])(=[O:16])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]1=2)[S:2]([CH3:1])(=[O:4])=[O:3])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19365895butyl-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)-amine

Product 1

HCID 9926984N-butyl-N-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)methanesulfonamideYield 106%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.63 g (57 mmol) of methanesulfonyl chloride were added dropwise to a solution of 11.7 g (41 mmol) of butyl-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)-amine and 15.5 g (153 mmol) of triethylamine in 120 ml of THF, and the reaction mixture was stirred at RT overnight. Most of the THF was distilled off, the residue was diluted with 250 ml of water and the precipitate was filtered off with suction. Drying under reduced pressure gave 13.8 g of N-butyl-N-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)methanesulfonamide; m.p. 171-173° C.

Workup

  1. distillationMost of the THF was distilled off
  2. additionthe residue was diluted with 250 ml of water
  3. filtrationthe precipitate was filtered off with suction
  4. customDrying under reduced pressure

Sources & evidence

ORD record
ord-bcf82f76bd3643cc9432f50bec656db2
Source dataset
uspto-grants-2000_01
Patent number
US06015822

Reaction notes

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