Nitric Acid → 2-Chloro-7-nitro-6-trifluoromethoxybenzothiazole
Reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:8]=[CH:7][C:5]=2[N:6]=1.[N+:16]([O-])([OH:18])=[O:17]>S(=O)(=O)(O)O>[Cl:1][C:2]1[S:3][C:4]2[C:10]([N+:16]([O-:18])=[O:17])=[C:9]([O:11][C:12]([F:15])([F:13])[F:14])[CH:8]=[CH:7][C:5]=2[N:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
10 g of 2-chloro-6-trifluoromethoxybenzothiazole are added dropwise over one hour to a mixture, cooled to 10° C., of concentrated sulphuric acid (50 cm3) and concentrated nitric acid (25 cm3). The mixture is then heated for one hour at 60° C. After cooling, the mixture is poured into an ice/water mixture (1/1 by weight) and extracted with 3 times 100 cm3 of chloroform. The organic phases are dried over magnesium sulphate and concentrated under vacuum (2.7 kPa). The residue is purified by flash chromatography with a chloroform/cyclohexane mixture (4/6 by volume) as eluent. 6.4 g of 2-chloro-7-nitro-6-trifluoromethoxybenzothiazole are thus obtained, melting at 64° C.
Workup
- temperatureAfter cooling
- extractionextracted with 3 times 100 cm3 of chloroform
- dry with materialThe organic phases are dried over magnesium sulphate
- concentrationconcentrated under vacuum (2.7 kPa)
- customThe residue is purified by flash chromatography with a chloroform/cyclohexane mixture (4/6 by volume) as eluent
Sources & evidence
- ORD record
- ord-9e5abc2d71cc473dbcba467b15ac9a7b
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05567822
Reaction notes
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