Nitric Acid → N-(5-(6-chloro-3-pyridazinyloxy)-2-nitrophenyl)-1,1,1-trifluoromethanesulfonamide

HRID 67161Notes

Reaction equation

HRID 67161 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:15][S:16]([C:19]([F:22])([F:21])[F:20])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[N+:23]([O-])([OH:25])=[O:24]>>[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([N+:23]([O-:25])=[O:24])=[C:11]([NH:15][S:16]([C:19]([F:20])([F:21])[F:22])(=[O:18])=[O:17])[CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 13052568HCID 13052568, compound

Product 1

HCID 20528762N-(5-(6-chloro-3-pyridazinyloxy)-2-nitrophenyl)-1,1,1-trifluoromethanesulfonamide

Conditions

Temperature
4 °C

Procedure

15 g of 1 was added in portions to 200 ml of chilled (4°-5° C.), stirred 90% nitric acid, and the mixture was stirred at 4° C. for 30 minutes. The resulting mixture was poured into ice water and the resulting solid was filtered. The filter cake was washed with water and purified by silica gel column chromatography, using as eluent a 66:30:4 (v:v:v) mixture of hexane, ethyl acetate and tetrahydrofuran, to give 2, as an amber glassy solid.

Workup

  1. temperatureof chilled (4°-5° C.)
  2. filtrationthe resulting solid was filtered
  3. washThe filter cake was washed with water
  4. custompurified by silica gel column chromatography
  5. additiona 66:30:4 (v:v:v) mixture of hexane, ethyl acetate and tetrahydrofuran
  6. customto give 2

Sources & evidence

ORD record
ord-707481f0b73e45cb946d5c2aad8239dd
Source dataset
uspto-grants-1982_08
Patent number
US04345077

Reaction notes

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