Water → HCID 178504626, compound

HRID 1973247Notes

Reaction equation

HRID 1973247 reaction equation
[N:1]([O-])=O.[Na+].O.S(=O)(=O)(O)O.[CH3:11][S:12]([CH2:14][C:15]1[C:16](=[CH:18][CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[NH2:17])=[O:13]>C(O)CC>[CH3:11][S:12]([C:14]1[C:15]2[C:16](=[CH:18][CH:19]=[C:20]([C:22]([F:23])([F:24])[F:25])[CH:21]=2)[NH:17][N:1]=1)=[O:13]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 9964708Benzenamine, 2-[(methylsulfinyl)methyl]-4-(trifluoromethyl)-HCID 23668193Sodium Nitrite

Product 1

HCID 178504626HCID 178504626, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

To a cooled (ice/water) solution of 3.7 g. of sodium nitrite predissolved in 20 ml. of water is slowly added 50 ml. of 3N sulfuric acid. To the resulting cooled (ice/water) solution is added dropwise, over a period of 30 minutes, a solution of 12.0 g. of a α-methylsulfinyl-4-trifluoromethyl-o-toluidine predissolved in 200 ml. of 1-propanol, while the temperature is maintained below 10° C. After the reaction mixture is stirred with cooling for an additional 90 minutes, it is allowed to stand overnight at room temperature. The reaction mixture is then nearly concentrated to dryness under vacuum and taken up in 100 ml. of chloroform and 60 ml. of a 15% sodium hydroxide solution. After separation of the phases, the aqueous phase is acidified with concentrated hydrochloric acid and the resulting precipitate filtered off. The acidified aqueous phase is washed three times with chloroform and the combined chloroform extracts are dried over potassium carbonate to a solid. Recrystallization of the crude product from chloroform/hexane yields 3-methylsulfinyl-5-trifluoromethyl indazole, m.p. 168°-170° C.

Workup

  1. additionis added dropwise, over a period of 30 minutes
  2. temperaturewith cooling for an additional 90 minutes
  3. concentrationThe reaction mixture is then nearly concentrated to dryness under vacuum
  4. customAfter separation of the phases
  5. filtrationthe resulting precipitate filtered off
  6. washThe acidified aqueous phase is washed three times with chloroform
  7. dry with materialthe combined chloroform extracts are dried over potassium carbonate to a solid
  8. customRecrystallization of the crude product from chloroform/hexane

Sources & evidence

ORD record
ord-1a996353b9b7410682a566eeea6a01dc
Source dataset
uspto-grants-1976_12
Patent number
US03996371

Reaction notes

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