Formaldehyde → 1-Phthalimido-2-[2-(5-dimethylaminomethyl-2-furyl)ethylthio]ethane

HRID 65742Notes

Reaction equation

HRID 65742 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][S:8][CH2:9][CH2:10][N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21].Cl.[CH3:23][NH:24][CH3:25].[CH2:26]=O>C(O)C>[CH3:23][N:24]([CH2:26][C:5]1[O:1][C:2]([CH2:6][CH2:7][S:8][CH2:9][CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[CH:3][CH:4]=1)[CH3:25]

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 10473Dimethylamine, hydrochloride2×HCID 234521132-[[2-(2-Furanyl)ethyl]thio]ethyl-1H-isoindole-1,3(2H)-dione

Product 1

HCID 234521761-Phthalimido-2-[2-(5-dimethylaminomethyl-2-furyl)ethylthio]ethaneYield 72.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[[2-(2-Furanyl)ethyl]thio]ethyl-1H-isoindole-1,3(2H)-dione (0.5 g), dimethylamine hydrochloride (0.27 g) and paraformaldehyde (0.102 g) were heated together under reflux in ethanol. After 5 hr further dimethylamine hydrochloride (0.27 g) and paraformaldehyde (0.102 g) were added and the heating continued for a further 16 hr. Solvent was removed, the residue basified and extracted with ethyl acetate to give an oil which after column chromatography (silica/methanol) gave 2-[2-[[2-[5-(dimethylamino)methyl-2-furanyl]ethyl]thio]ethyl]-1H-isoindole-1,3(2H)dione as a pale oil (0.43 g). Analysis Found: C, 61.48; H, 6.13; N, 7.63; C19H22N2O3S.3 /4H2O requires: C, 61.35; H, 6.37; N, 7.53%.

Workup

  1. customSolvent was removed
  2. extractionextracted with ethyl acetate
  3. customto give an oil which after column chromatography (silica/methanol)

Sources & evidence

ORD record
ord-634f5e10e6c442b4baa103e8faa0f232
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

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