Nitric Acid → 4-Chloro-6-fluoro-2-methyl-7-nitrobenzothiazole

HRID 1419710Notes

Reaction equation

HRID 1419710 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Cl:5][C:6]1[C:11]2[N:12]=[C:13]([CH3:15])[S:14][C:10]=2[CH:9]=[C:8]([F:16])[CH:7]=1>S(=O)(=O)(O)O>[Cl:5][C:6]1[C:11]2[N:12]=[C:13]([CH3:15])[S:14][C:10]=2[C:9]([N+:1]([O-:4])=[O:2])=[C:8]([F:16])[CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 53871027HCID 53871027, compound

Product 1

HCID 537041054-Chloro-6-fluoro-2-methyl-7-nitrobenzothiazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

A solution of 7 ml of concentrated nitric acid in 6 ml of concentrated sulfuric acid was added to a solution of 10 g (50 mmol) of 4-chloro-6-fluoro-2-methylbenzothiazole in 35 ml of concentrated sulfuric acid. Stirring was carried out for 10 minutes, after which the mixture was poured into ice water. Thereafter, the suspended desired product was separated off and, for purification, was dissolved in 100 ml of 3:1 cyclohexane/ethyl acetate. After filtration over a bed of silica gel, 8 g of desired product was obtained from the remaining solution; mp.: 130° to 132° C.

Sources & evidence

ORD record
ord-633bac0459264608854c6434baf53f2a
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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