Tetrahydrofuran → beta-Hydroxy-ethyl 1,4-dihydro-2,6-dimethyl-3-nitro-4-(2-chlorophenyl)-pyridine-5-thiocarboxylate
Reaction equation
[N-]1C=CN=C1.[CH3:6][C:7]1[NH:8][C:9]([CH3:26])=[C:10]([C:23]([OH:25])=O)[CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:12]=1[N+:13]([O-:15])=[O:14].[SH:27]C(O)C.[O:31]1CC[CH2:33][CH2:32]1>>[CH3:6][C:7]1[NH:8][C:9]([CH3:26])=[C:10]([C:23](=[S:27])[O:25][CH2:33][CH2:32][OH:31])[CH:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[C:12]=1[N+:13]([O-:15])=[O:14]Participants
4
Procedure
3 g of 1,4-dihydro-2,6-dimethyl-3-nitro-4-(2-chlorophenyl)-pyridine-5-carboxylic acid imidazolide are boiled in 12.5 ml of absolute tetrahydrofuran with 5 ml of mercaptoethanol for 7 hours. The mixture is concentrated, the concentrate is concentrated at 70° C. using an oil pump, the residue is dissolved in chloroform and the solution is washed twice with water, dried and concentrated. The resulting evaporation residue is purified over a silica gel column with a volume of 160 ml, using toluene and later toluene/ethyl acetate 6:1 as the mobile phase. 1.94 g of a yellow foam with an Rf value of 0.25 are obtained as the main fraction.
Workup
- concentrationThe mixture is concentrated
- concentrationthe concentrate is concentrated at 70° C.
- dissolutionthe residue is dissolved in chloroform
- washthe solution is washed twice with water
- customdried
- concentrationconcentrated
- customThe resulting evaporation residue
- customis purified over a silica gel column with a volume of 160 ml
Sources & evidence
- ORD record
- ord-a1da68f051494cb081b5b6e4331cbe71
- Source dataset
- uspto-grants-1987_02
- Patent number
- US04645775
Reaction notes
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