Ethanol → HCID 12822508, compound

HRID 980291Notes

Reaction equation

HRID 980291 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH2:13][NH:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=2)[NH:6][CH:5]=1.[CH2:19]([OH:21])C>C(OCC)=O>[CH3:18][S:15]([NH:14][CH2:13][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][CH:5]=[C:4]2[CH2:3][CH2:2][NH:1][CH:19]=[O:21])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 702EthanolHCID 12822471HCID 12822471, compound

Product 1

HCID 12822508HCID 12822508, compound

Reagents, catalysts & solvents 1

HCID 8025Ethyl formateSolvent

Procedure

A solution of N-[[3-(2-aminoethyl)-1H-indol-5-yl]methyl]methanesulphonamide (2.1 g) in ethanol (20 ml) and ethyl formate (25 ml) was refluxed for 17 h. The solvent was evaporated in vacuo and the residue was partitioned between sulphuric acid (1N; 100 ml) and ethyl acetate (150 ml). The aqueous layer was extracted with ethyl acetate (150 ml) and the combined organic extracts were washed with brine (50 ml) and potassium carbonate solution (15%; 50 ml) and dried (Na2SO4). Evaporation of the solvent in vacuo gave the crude product as a very viscous oil (2.2 g). The oil was dissolved in THF (8 ml), scratched and left overnight at room temperature. Filtration gave the title compound (1.3 g) as a white solid m.p. 121°-5°.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between sulphuric acid (1N; 100 ml) and ethyl acetate (150 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (150 ml)
  4. washthe combined organic extracts were washed with brine (50 ml) and potassium carbonate solution (15%; 50 ml)
  5. dry with materialdried (Na2SO4)
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-0ac6db0a320a4967ba188ab6e8030e40
Source dataset
uspto-grants-1987_01
Patent number
US04636521

Reaction notes

Loading…