Formaldehyde → HCID 10358221, compound

HRID 728178Notes

Reaction equation

[CH2:1]([N:3]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[CH:12]=[CH:11][C:9]=2[N:10]=1)C=O)[CH3:2].[CH2:22]=O.Cl.[CH3:25][NH:26][CH3:27]>C(O)(=O)C>[CH3:25][N:26]([CH2:22][C:19]1[O:18][C:17]([CH2:16][CH2:15][C:13]2[CH:12]=[CH:11][C:9]3[N:10]=[C:6]([NH:3][CH2:1][CH3:2])[O:7][C:8]=3[CH:14]=2)=[CH:21][CH:20]=1)[CH3:27]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 2-(N-ethylformamido)-6-[2-(2-furyl)ethyl]benzoxazole (1.25 g), 36% formalin (1.83 ml) and dimethylamine hydrochloride (1.79 g) in acetic acid (8.3 ml) was stirred at 80° C. for 6 hours. The solvent was evaporated in vacuo, the residue was mixed with saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel by eluting with chloroform-methanol (20:1, V/V). The pure base was converted to the maleate in a usual way and the salt was recrystallized from ethyl acetate to give 6-[2-(5-dimethylaminomethylfuran- 2-yl)ethyl]-2-ethylaminobenzoxazole 3/2 maleate (0.38 g).

Workup

customThe solvent was evaporated in vacuo
additionthe residue was mixed with saturated aqueous sodium bicarbonate
extractionextracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel
washby eluting with chloroform-methanol (20:1, V/V)
customthe salt was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-6b54da25ac80421fa621499a876aa3c7
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047411

Reaction notes

Loading…