Acetic Acid → HCID 14233887, compound
Reaction equation
O[CH:2]([C:18]1[N:19]=[CH:20][N:21](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:22]=1[CH3:23])[CH:3]1[C:15](=[O:16])[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7]([CH3:17])[C:6]=2[CH2:5][CH2:4]1.O.C1(C)C=CC(S(O)(=O)=[O:51])=CC=1.[C:55]([OH:58])(=[O:57])[CH3:56]>>[C:15]([OH:16])(=[O:51])/[CH:3]=[CH:56]\[C:55]([OH:58])=[O:57].[CH3:17][N:7]1[C:6]2[CH2:5][CH2:4]/[C:3](=[CH:2]\[C:18]3[N:19]=[CH:20][NH:21][C:22]=3[CH3:23])/[C:15](=[O:16])[C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2Participants
Procedure
A solution of 1,2,3,9-tetrahydro-3-[hydroxy[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-9-methyl-4H-carbazol-4-one (2.70 g) in glacial acetic acid (100 ml) was treated with p-toluenesulphonic acid monohydrate (10.80 g) and the stirred solution heated at reflux for 4 h. The cool, dark liquid was evaporated, treated with aqueous saturated sodium bicarbonate (250 ml) and extracted into ethyl acetate (4×250 ml). the combined, dried organic extracts were evaporated, and purified by SPCC. Elution with System A (978:20:2→945:50:5) afforded the free base of the title compound as a light yellow-brown solid (488 mg). A hot solution of the free base (87 mg) in ethanol (ca. 16 ml) was treated with a hot solution of maleic acid (38 mg) in ethanol (1 ml), and on cooling the precipitate was collected to give the title compound (81 mg), m.p. 205°-209°.
Workup
- temperaturethe stirred solution heated
- temperatureat reflux for 4 h
- customThe cool, dark liquid was evaporated
- additiontreated with aqueous saturated sodium bicarbonate (250 ml)
- extractionextracted into ethyl acetate (4×250 ml)
- customdried organic extracts were evaporated
- custompurified by SPCC
- washElution with System A (978:20:2→945:50:5)
Sources & evidence
- ORD record
- ord-8276061ea63b4e8dac7506fa0e04c66a
- Source dataset
- uspto-grants-1989_08
- Patent number
- US04859662
Reaction notes
Loading…