Formaldehyde → HCID 57496010, compound

Participants

Reaction Conditions

Reaction Steps

Dimethyl 5-aminoisophthalate (1.00 g, 4.78 mmol, 1 eq) and glyoxal trimer 2H2O (1.004 g, 4.78 mmol, 1 eq) were stirred in 6 ml EtOH overnight. NH4Cl (0.5114 g, 9.56 mmol, 2 eq) was added. After 15 min aqueous formaldehyde (37%, 0.71 ml, 0.78 g, 9.56 mmol, 2 eq) was added and the mixture was heated to reflux at 90° C. After 1 h the reaction was cooled to room temperature. After the dropwise addition of H3PO4 (85%, 0.65 ml, 1.1 g, 9.56 mmol, 2 eq) the reaction was heated to reflux at 95° C. After 6 h the reaction was cooled to room temperature and the solvent was removed in vacuo. The residue was stirred in CHCl3 and the mixture was filtered through cotton to remove any insoluble material. Purification via flash chromatography yielded 0.7329 g (2.82 mmol, 59% yield) of dimethyl 5-(1H-imidazol-1-yl)isophthalate.

Provenance & Evidence