Butylamine → butyl-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)-amine

HRID 850021Notes

Reaction equation

HRID 850021 reaction equation
[S:1]1(=[O:11])(=[O:10])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH2:12]([NH2:16])[CH2:13][CH2:14][CH3:15]>C(O)C>[CH2:12]([NH:16][CH:3]1[CH2:2][S:1](=[O:10])(=[O:11])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]1=2)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 69997Benzothiophene 1,1-dioxide

Product 1

HCID 19365895butyl-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)-amineYield 112.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.0 g (54 mmol) of benzothiophene 1,1-dioxide and 7.9 g (108 mmol) of n-butylamine were suspended in 130 ml of ethanol, and the mixture was heated at reflux temperature for 3 h. The reaction mixture was concentrated under reduced pressure, giving 14.5 g of butyl-(1,1-dioxo-2,3-dihydro-1H-benzo[b]thiophen-3-yl)-amine as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 3 h
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fe8dc6222c34428e89d9228cec25f046
Source dataset
uspto-grants-2000_01
Patent number
US06015822

Reaction notes

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