Tetrahydrofuran → HCID 178481591, compound
Reaction equation
[N:1]1([CH2:6][C:7]2[CH:8]=[C:9](N)C(NC)=C[CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[C:16]([N:23]1[CH:27]=[CH:26][N:25]=[CH:24]1)(N1C=CN=C1)=O.[O:28]1CCCC1>>[N:1]1([CH2:6][C:7]2[CH:8]=[CH:9][C:27]3[N:23]([CH3:16])[C:24]([OH:28])=[N:25][C:26]=3[CH:12]=2)[CH:5]=[CH:4][N:3]=[CH:2]1Participants
Procedure
A mixture of 4.04 parts of 4-(1H-imidazol-1-ylmethyl)-N1 -methyl-1,2-benzenediamine, 3.6 parts of 1,1'-carbonylbis[1H-imidazole] and 80 parts of tetrahydrofuran was stirred for about 100 hours at room temperature. The formed precipitate was filtered off, washed with tetrahydrofuran, dried and purified twice by column chromatography over silica gel using each time a mixture of trichloromethane, methanol and methanol, saturated with ammonia (90:5:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The solid residue was crystallized from 2-propanol. The product was filtered off, washed with 2-propanol and 2,2'-oxybispropane, and dried, yielding 3.5 parts (77%) of 5-(1H-imidazol-1-ylmethyl)-1-methyl-1H-benzimidazol-2-ol; mp. 207.2° C. (compound 222).
Workup
- filtrationThe formed precipitate was filtered off
- washwashed with tetrahydrofuran
- customdried
- custompurified twice by column chromatography over silica gel using each time
- additiona mixture of trichloromethane, methanol and methanol
- customThe pure fractions were collected
- customthe eluent was evaporated
- customThe solid residue was crystallized from 2-propanol
- filtrationThe product was filtered off
- washwashed with 2-propanol and 2,2'-oxybispropane
- customdried
Sources & evidence
- ORD record
- ord-27fc7d99a5df4cdc82428cde7afbeeee
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04859684
Reaction notes
Loading…