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

HRID 1277994Notes

Reaction equation

HRID 1277994 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-64638b4c508b45e9b6daad661d61f34c
Source dataset
uspto-grants-1981_07
Patent number
US04279911

Reaction notes

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