Dimethylformamide → HCID 178458205, compound
Reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[C:9]([C:11](SC)=[NH:12])[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[N:6]=1)([CH3:3])[CH3:2].[CH:19]([NH:21]N)=O.C[N:24](C=O)C>>[CH:1]([O:4][C:5]1[CH:10]=[C:9]([C:11]2[N:21]=[CH:19][NH:24][N:12]=2)[CH:8]=[C:7]([C:15]([F:18])([F:17])[F:16])[N:6]=1)([CH3:3])[CH3:2]Participants
Procedure
In a 50 ml capacity 3-neck round-bottomed flask attached with nitrogen bubbler, reflux condenser & magnetic stirrer methyl 2-isopropoxy-6-(trifluoromethyl)pyridine-4-carbimidothioate (5 g), formic hydrazide (0.431), dissolved in 50 ml DMF at RT for 20 min to form uncyclised form of 2-isopropoxy-4-(1H-1,2,4-triazol-3-yl)-6-(trifluoromethyl)pyridine which was confirmed by mass and on TLC as a polar spot as compared to starting material. Heated the reaction mixture at 80-90° C. for 6 h, which gave a non polar spot as compared to uncyclised form. The completion of the reaction was confirmed by TLC with 50% EtOAc-hexane as mobile phase. The reaction mixture was poured in ice water solution & extract with ethyl acetate (3×200 ml). Organic layer dried over Na2SO4 and concentrated to give crude product (5 g). The crude reaction mixture was purified by column chromatography using silica 60/120 using ethyl acetate:hexane as mobile phase. The column was packed in hexane and started eluting in ethyl acetate in gradient manner starting with fraction collection (25-mL fractions) from 5% to 25% ethyl acetate in hexane. Compound started eluting with 25% ethylacetate in hexane. Fraction containing such TLC profile was collected together to obtain pure 2-isopropoxy-4-(1H-1,2,4-triazol-3-yl)-6-(trifluoromethyl)pyridine (3.5 g).
Workup
- customIn a 50 ml capacity 3-neck round-bottomed flask attached with nitrogen bubbler
Sources & evidence
- ORD record
- ord-ca6a951bc9a44b51998a93b720afcda7
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09303000B2
Reaction notes
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