Sulfuric Acid → 4-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridazin-3-ylamine

HRID 2237923Notes

Reaction equation

HRID 2237923 reaction equation
COC1C=CC(C[NH:8][C:9]2[N:10]=[N:11][C:12]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:13][C:14]=2[C:15]([F:18])([F:17])[F:16])=CC=1.OS(O)(=O)=O>>[F:18][C:15]([F:16])([F:17])[C:14]1[CH:13]=[C:12]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)[N:11]=[N:10][C:9]=1[NH2:8]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 86608020(4-Methoxy-benzyl)-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridazin-3-yl]-amine

Product 1

HCID 866080224-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridazin-3-ylamine

Conditions

Temperature
5 °C

Procedure

(4-Methoxy-benzyl)-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridazin-3-yl]-amine (example C.26 step 8) (6.48 g, 15 mmol) was added portionwise at 5° C. to conc. H2SO4 (d 1.83, 17.0 mL, 303 mmol). The deep purple solution was stirred for 5 min at 5° C. then the cooling bath was removed and stirring was continued for further 60 min at 23° C. The mixture was poured onto ice, made alkaline with 32% NaOH-sol., saturated with solid NaCl and extracted with THF and TBME, dried the organic layer over MgSO4. Removal of the solvent in vacuum left the title compound as a light yellow solid (4.44 g, 95%), which was used without further purification. MS (ISP) 308.1 [(M+H)+]; mp 186-190° C.

Workup

  1. customthe cooling bath was removed
  2. stirringstirring
  3. waitwas continued for further 60 min at 23° C
  4. additionThe mixture was poured onto ice
  5. extraction, saturated with solid NaCl and extracted with THF and TBME
  6. dry with materialdried the organic layer over MgSO4
  7. customRemoval of the solvent in vacuum
  8. waitleft the title compound as a light yellow solid (4.44 g, 95%), which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-b92c6848e92d4b11ab9586f3300ba904
Source dataset
uspto-grants-2010_05
Patent number
US07718661B2

Reaction notes

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