Ammonia → 10-Acetamido-10-(3-chlorophenyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indole
Reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2(O)[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]3[CH2:22][CH2:23][CH2:24][N:25]=[C:14]23)[CH:10]=[CH:11][CH:12]=1.N.[C:28](#[N:30])[CH3:29]>>[C:28]([NH:30][C:13]1([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=2)[C:21]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:15]2[CH2:22][CH2:23][CH2:24][N:25]=[C:14]12)(=[O:2])[CH3:29]Participants
Procedure
Concentrated sulphuric acid (12 ml) was added dropwise over 5 minutes to vigorously stirred acetonitrile (24 ml) at 0°-5°. The resulting colourless solution was treated in one portion with 10-(3-chlorophenyl)-2,3,4,10-tetrahydropyrimido[1,2-a]indol -10-ol (3.0 g). The mixture was immediately stirred and heated at 50°-60° whereupon solution occurred within 5 minutes. After 1 hour, the solution was poured onto ice (100 ml) and the mixture was basified with saturated aqueous ammonia (90 ml) and extracted with dichloromethane (3×60 ml). The extracts were dried (MgSO4) and evaporated in vacuo. The residue was triturated with ethyl acetate to give light brown crystals which were purified by flash chromatography (Al2O3, ethyl acetate), trituration with ethanol-ether (1:1), and washing with ether to give the title compound free base as a colourless powder.
Workup
- temperatureheated at 50°-60° whereupon solution
- waitAfter 1 hour
- additionthe solution was poured onto ice (100 ml)
- extractionextracted with dichloromethane (3×60 ml)
- dry with materialThe extracts were dried (MgSO4)
- customevaporated in vacuo
- customThe residue was triturated with ethyl acetate
- customto give light brown crystals which
- customwere purified by flash chromatography (Al2O3, ethyl acetate), trituration with ethanol-ether (1:1)
- washwashing with ether
Sources & evidence
- ORD record
- ord-462a350c926b4fc38d7fda19eab91743
- Source dataset
- uspto-grants-1988_11
- Patent number
- US04783455
Reaction notes
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