Methanol → N-(prop-2-yn-1-yl)benzenesulfonamide

HRID 1834737Notes

Reaction equation

HRID 1834737 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([S:7]([NH:10]O)(=[O:9])=[O:8])=[CH:3][CH:2]=1.CO.[CH2:14](Br)[C:15]#[CH:16].C[O-].[Na+]>CCOCC>[CH2:16]([NH:10][S:7]([C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)(=[O:9])=[O:8])[C:15]#[CH:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 7842Propargyl bromideHCID 69033N-HydroxybenzenesulfonamideHCID 10942334Sodium Methoxide

Product 1

HCID 11287036N-(prop-2-yn-1-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
30 °C

Procedure

To 8.6 g. piloty acid dissolved in 50 ml. methanol, propargyl bromine (6.6 g.) was added. 10.8 g. sodium methoxide (25%) was added slowly dropwise. An exothermic reaction resulted, the temperature was maintained at 30° C. The reaction mixture was stirred for approximately 1 hour at room temperature. The solvent was removed in vacuo. There was obtained a yellow solid. This material was treated with ether and the solid filtered off and dried. There was obtained 3.1 g. of the title compound, a low melting solid.

Workup

  1. customAn exothermic reaction
  2. customresulted
  3. customThe solvent was removed in vacuo
  4. customThere was obtained a yellow solid
  5. filtrationthe solid filtered off
  6. customdried
  7. customThere was obtained 3.1 g

Sources & evidence

ORD record
ord-185b609c225b40e29b8bdde0012ce313
Source dataset
uspto-grants-1978_01
Patent number
US04071350

Reaction notes

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