Fumaric Acid → HCID 131715266, compound
Reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].C(O)(=O)/C=C/C(O)=O.[CH3:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[NH:25][C:26](=O)[CH2:27][CH2:28][CH2:29][N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1>CO.CCOCC>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[CH3:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH3:17])[C:19]=1[NH:25][CH2:26][CH2:27][CH2:28][CH2:29][N:30]1[CH:34]=[CH:33][N:32]=[CH:31]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 27.27 g of N-(2,6-dimethylphenyl)-1H-imidazole-butanamide hydrobromide salt in 250 ml of dry tetrahydrofuran was added dropwise with stirring to 530 ml of 1 molar borane in tetrahydrofuran and the resulting solution was heated to reflux for 2 hours. After cooling, excess methanol was added to decompose the remaining borane and the solution was evaporated to dryness. The residue was acidified by the cautious addition of 285 ml of 2N hydrochloric acid and was warmed on the steam bath for 20 minutes. The resulting solution was cooled, made strongly basic with sodium hydroxide solution and was extracted with dichloromethane. The combined organic layers were dried with potassium carbonate and concentrated to give 25.1 g of N-(2,6-dimethylphenyl)-1H-imidazole-1-butanamine as an oil which was dissolved in 200 ml of methanol, treated with 23.9 g of fumaric acid and diluted with 600 ml of ether. The resulting solid amounted to 37.0 g of N-(2,6-dimethylphenyl)-1H-imidazole-1-butanamide (E)-2-butenedioate(1:2) salt, mp 146°-147° C. Recrystallization from methanol-ether gave the analytical sample, mp 148°-149° C.
Workup
- customRecrystallization from methanol-ether
- customgave the analytical sample, mp 148°-149° C.
Sources & evidence
- ORD record
- ord-2ac10125f6564ab896ddd84c217fed9e
- Source dataset
- uspto-grants-1987_09
- Patent number
- US04696930
Reaction notes
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