Dimethylformamide → HCID 21451965, compound
Reaction equation
CO[C:3]1[CH:26]=[CH:25][CH:24]=[CH:23][C:4]=1[C:5]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)=[O:6].[Na].[H-].[Na+].Br[C:31]([CH3:38])([CH3:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33].CN(C)[CH:41]=[O:42]>>[CH3:37][C:31]([O:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][CH2:8][NH:7][C:5](=[O:6])[C:4]3[CH:23]=[CH:24][C:25]([O:42][CH3:41])=[CH:26][CH:3]=3)=[CH:11][CH:12]=2)=[CH:17][CH:18]=1)([CH3:38])[C:32]([O:34][CH2:35][CH3:36])=[O:33]Participants
6
Procedure
7.4 gm (21.2 millimols) of 4-[2-(4-methoxy-benzamido)-ethyl]-4'-hydroxy-biphenyl (see Example I) were dissolved in 60 ml of absolute dimethyl formamide and converted into the sodium salt with 1.1 gm (about 25 millimols) of 55% sodium hydride suspension in oil, and the salt was reacted with 9.7 gm (51.5 millimols) of ethyl 2-bromo-2-methyl-propionate at room temperature over a period of 18 hours. After distilling off the dimethylformamide, the evaporation residue was dissolved in acetone, the solution was filtered, the acetone was distilled out of the filtrate, and the residue was purified on a silicagel column with toluene/ethyl acetate (4:1) as the eluant. Yield: 2 gm (20% of theory); m.p. 149°-150° C.
Workup
- distillationAfter distilling off the dimethylformamide
- dissolutionthe evaporation residue was dissolved in acetone
- filtrationthe solution was filtered
- distillationthe acetone was distilled out of the filtrate
- customthe residue was purified on a silicagel column with toluene/ethyl acetate (4:1) as the eluant
Sources & evidence
- ORD record
- ord-df4e2051c6af4567be7266748f4c9e72
- Source dataset
- uspto-grants-1977_03
- Patent number
- US04010279
Reaction notes
Loading…