Formaldehyde → HCID 23452116, compound

HRID 65746Notes

Reaction equation

HRID 65746 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:20].[CH2:21]=O.Cl.[CH3:24][NH:25][CH3:26]>C(O)C>[CH3:24][N:25]([CH2:21][C:5]1[O:1][C:2]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])=[CH:3][CH:4]=1)[CH3:26]

Participants

5

Reactant 3

HCID 712Formaldehyde2×HCID 10473Dimethylamine, hydrochloride2×HCID 23452135HCID 23452135, compound

Product 1

HCID 23452116HCID 23452116, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[4-(2-Furanyl)butyl]-1H-isoindole-1,3(2H)-dione (5.38 g), paraformaldehyde (1.2 g) and dimethylamine hydrochloride (3.26 g) were refluxed in absolute ethanol (100 ml). After 6 hr further paraformaldehyde (0.6 g) and dimethylamine hydrochloride (1.6 g) were added and heating continued for a further 20 hr. The solvent was removed, the residue made strongly basic with 5N sodium hydroxide, extracted with ethyl acetate and the organic layer evaporated. The crude product was purified by column chromatography to give an amber oil (3.25 g) Rf 0.4 silica/methanol. NMR (CDCl3) 8-8.6 m (4H); 7.75 s (6H); 7.3 m (2H); 6.55 s (2H); 6.3 m (2H); 4.0 m (2H); 1.9-2.4 m (4H).

Workup

  1. temperatureheating
  2. customThe solvent was removed
  3. extractionextracted with ethyl acetate
  4. customthe organic layer evaporated
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-cc5163ad0c4e4f93a38f78542f4ad5ef
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

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