Nitric Acid → 2,4-Dichloro-6-fluoro-7-nitrobenzothiazole

HRID 21724Notes

Reaction equation

HRID 21724 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[C:7]([Cl:12])[C:5]=2[N:6]=1.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[Cl:1][C:2]1[S:3][C:4]2[C:10]([N+:13]([O-:15])=[O:14])=[C:9]([F:11])[CH:8]=[C:7]([Cl:12])[C:5]=2[N:6]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 534405702,4-Dichloro-6-fluoro-1,3-benzothiazole

Product 1

HCID 199334652,4-Dichloro-6-fluoro-7-nitrobenzothiazole

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

23.7 g 2,4-Dichloro-6-fluorobenzothiazole was dissolved in 100 ml concentrated sulfuric acid and the solution cooled to 0° C. To this was added very slowly, dropwise, a cooled solution of 14 ml concentrated sulfuric acid and 14 ml 100% nitric acid. The mixture was stirred for 3 hours, poured into 500 ml ice water, the resulting crystals filtered off, washed with water until neutral and dried in vacuo. Yield: 22.7 g=79% of theory m.p.: 110°-112° C.

Workup

  1. additionTo this was added very slowly
  2. filtrationthe resulting crystals filtered off
  3. washwashed with water until neutral and
  4. customdried in vacuo

Sources & evidence

ORD record
ord-87571bf49b2c43568c8a92beb534f448
Source dataset
uspto-grants-1995_06
Patent number
US05424443

Reaction notes

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