Sodium Hydroxide → Ethyl 1-(carbamothioylmethyl)-1H-pyrazole-4-carboxylate
Reaction equation
[C:1]([CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1)#[N:2].C(OCC)(=O)C.Cl.P([O-])(OCC)(SCC)=[S:22].C(=O)([O-])O.[Na+].[OH-].[Na+]>>[NH2:2][C:1](=[S:22])[CH2:3][N:4]1[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[N:5]1Participants
6
Procedure
To the compound (1.14 g, 6.34 mmol) obtained in Example 1a were added 4M hydrogen chloride-ethyl acetate solution (12 mL) and diethyl dithiophosphate (1.59 mL, 9.51 mmol), and the mixture was stirred for 23 hr. The reaction mixture was alkalified with saturated aqueous sodium hydrogen carbonate solution and 8N aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate, washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (0.98 g, 72%) as a colorless solid.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washwashed successively with water and saturated brine
- dry with materialdried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)
Sources & evidence
- ORD record
- ord-c691613b73db40d7a7f641cf8146a70a
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461348B2
Reaction notes
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