Sulfuric Acid → 6-(2-Chloro-4-trifluoromethylphenoxy)-1,2,3-benzothiadiazole

HRID 64558Notes

Reaction equation

HRID 64558 reaction equation
C([S:8][C:9]1[CH:15]=[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=2[Cl:27])[CH:13]=[CH:12][C:10]=1[NH2:11])C1C=CC=CC=1.S(=O)(=O)(O)O.[N:33]([O-])=O.[Na+]>O>[Cl:27][C:18]1[CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=[CH:22][C:17]=1[O:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]=[N:33][S:8][C:9]=2[CH:15]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 202362802-Benzylthio-4-(2-chloro-4-trifluoromethylphenoxy)anilineHCID 23668193Sodium Nitrite

Product 1

HCID 202362796-(2-Chloro-4-trifluoromethylphenoxy)-1,2,3-benzothiadiazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3 g of 1C was added to an ice-cold solution of 50% aqueous sulfuric acid, and the mixture maintained below 10° C. during the addition of a solution of 0.7 g of sodium nitrite in 10 ml of water. This mixture was then stirred for 1 hour, allowed to reach ambient temperature, and then extracted with ether. The organic layer was separated, solvent removed and the resulting red oil chromatographically purified and recrystallized to yield 1, as a crystalline solid, m.p.: 72°-73° C.

Workup

  1. customto reach ambient temperature
  2. extractionextracted with ether
  3. customThe organic layer was separated
  4. customsolvent removed
  5. customthe resulting red oil chromatographically purified
  6. customrecrystallized
  7. customto yield 1

Sources & evidence

ORD record
ord-790d55d6419040eaac72634241915ea5
Source dataset
uspto-grants-1986_09
Patent number
US04609394

Reaction notes

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