Hydrogen Sulfide → HCID 54366048, compound
Reaction equation
ClC(C1C(CC2CC2)=C(C(OC)=O)C(C(F)F)=NC=1C(F)(F)F)=O.[CH:25]1([CH2:28][C:29]2[C:34]([C:35]#[N:36])=[C:33]([C:37]([F:40])([F:39])[F:38])[N:32]=[C:31]([CH:41]([F:43])[F:42])[C:30]=2[C:44]([O:46][CH3:47])=[O:45])[CH2:27][CH2:26]1.C(NCC)C.[SH2:53]>CN(C=O)C>[NH2:36][C:35](=[S:53])[C:34]1[C:29]([CH2:28][CH:25]2[CH2:27][CH2:26]2)=[C:30]([C:44]([O:46][CH3:47])=[O:45])[C:31]([CH:41]([F:43])[F:42])=[N:32][C:33]=1[C:37]([F:40])([F:38])[F:39]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Methyl 5-chlorocarbonyl-4-(cyclopropylmethyl)-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridine-carboxylate (example B3 of U.S. Pat. No. 5,156,670) was converted to methyl 4-(cyclopropylmethyl)-5-cyano-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridine-carboxylate by the procedure similar to example 88 and 92 of U.S. Pat. No. 4,692,184. A solution of 20 g (60 mmol) of this cyano compound and 0.62 g (6 mmol) of diethylamine in 60 ml of DMF was heated to 50° C. Hydrogen sulfide gas was introduced into this solution. When absorption of hydrogen sulfide was complete the reaction mixture was stirred at 50° C. for 1 h and poured into water and extracted with ether. The ether extract was washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was kugelrohr distilled to give 17.7 g (80% yield) of yellow oil.
Workup
- customWhen absorption of hydrogen sulfide
- additionpoured into water
- extractionextracted with ether
- extractionThe ether extract
- washwas washed with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- distillationThe residue was kugelrohr distilled
Sources & evidence
- ORD record
- ord-2612239ff1954386b704c760b0a1ce00
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06605624B1
Reaction notes
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