Methylamine → (5-{[(2-Aminoethyl)sulfanyl]methyl}furan-2-yl)methanol

HRID 1659575Notes

Reaction equation

HRID 1659575 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([CH2:8][S:9][CH2:10][CH2:11][N:12]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:5][CH:4]=1.CN>C(O)C>[OH:1][CH2:2][C:3]1[O:7][C:6]([CH2:8][S:9][CH2:10][CH2:11][NH2:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 20559413HCID 20559413, compound

Product 1

HCID 14234538(5-{[(2-Aminoethyl)sulfanyl]methyl}furan-2-yl)methanolYield 45.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[2-[[5-(hydroxymethyl)-2-furanylmethyl]thio]ethyl]-1H-isoindole-1,3(2H)-dione (5.0 g) in ethanol (50 ml) was stirred in the presence of methylamine (33% in ethanol) (15 ml) for 15 mins. The residue was subjected to column chromatography (silica/methanol-ethyl acetate 1:1, then methanol) and the appropriate eluates were evaporated. Chloroform (50 ml) was added to the oily product, the solution dried (anhyd. magnesium sulphate) and evaporated yielding the title compound as a pale yellow oil (1.35 g).

Workup

  1. custommethanol) and the appropriate eluates were evaporated
  2. additionChloroform (50 ml) was added to the oily product
  3. dry with materialthe solution dried (anhyd. magnesium sulphate)
  4. customevaporated

Sources & evidence

ORD record
ord-a76201c7bfce4d87a61c25a5faa17d34
Source dataset
uspto-grants-1981_12
Patent number
US04304780

Reaction notes

Loading…