Sulfuric Acid → HCID 68804027, compound

HRID 2099041Notes

Reaction equation

HRID 2099041 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]#N)[C:3]=1S(C(F)(F)F)=O.S(=O)(=O)(O)[OH:28].[OH-:32].[Na+]>>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([C:19]([OH:28])=[O:32])[CH:3]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 3352FipronilHCID 14798Sodium Hydroxide

Product 1

HCID 68804027HCID 68804027, compoundYield 77%

Conditions

Temperature
135 °C

Procedure

A stirred mixture of 5-amino-1 -(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfinyl-1 H-pyrazole-3-carbonitrile (5.00 g, 11.4 mmol) and sulfuric acid (50%, 100 ml) was heated to 135° C. for 3 hours. The cooled mixture was added to ice water and the pH adjusted to 4 by the addition of aqueous sodium hydroxide (6 N, approx. 230 ml), and then extracted with ethyl acetate. The organic phase was dried over magnesium sulfate, evaporated to dryness and purified by flash chomatography (silica, chloroform/ethanol) with subsequently trituration with tetrachloromethane to give the title compound (3.00 g, yield 77%) as off-white crystals, mp 213° C., 1H NMR (DMSO-d6): 5.69 (bs, 2H, NH2), 5.76 (s, 1H, pyrazole-H), and 8.20 (s, 2H, Ar—H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customevaporated to dryness
  4. custompurified by flash chomatography (silica, chloroform/ethanol) with subsequently trituration with tetrachloromethane

Sources & evidence

ORD record
ord-ed6374a914874b30bd34fbdf0dca232b
Source dataset
uspto-grants-2009_08
Patent number
US07569516B2

Reaction notes

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