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

HRID 224638Notes

Reaction equation

HRID 224638 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-0fea02d66c464fe28b8b411cfc73a0c6
Source dataset
uspto-grants-1980_11
Patent number
US04233302

Reaction notes

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