Sulfuric Acid → 5-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-1H-pyrazole-3-carboxylic acid amide

HRID 2099040Notes

Reaction equation

HRID 2099040 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:20])[C:3]=1[S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22].S(=O)(=O)(O)[OH:29]>>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:16])([F:17])[F:15])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]([NH2:20])=[O:29])[C:3]=1[S:21]([C:24]([F:26])([F:25])[F:27])(=[O:23])=[O:22]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 3078139Fipronil sulfone

Product 1

HCID 154569455-Amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-1H-pyrazole-3-carboxylic acid amideYield 83%

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoromethylsulfonyl-1 H-pyrazole-3-carbonitrile (1.06 g, 2.21 mmol) and concentrated sulfuric acid (1 ml) was heated to 100° C. for 3 hours. The cooled mixture was added to ice water and the precipitate filtered off, washed with water and air-dried. Purification by flash chomatography (silica, chloroform) gave the title compound (0.869 g, yield 83%) as off-white crystals, mp 217° C., 1H NMR (DMSO-d6): 7.39 (bs, 2H, NH2), 7.57 and 7.78 (bs, 2H, C(O)NH2), and 8.25 (s, 2H, Ar—H).

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed with water
  3. customair-dried
  4. customPurification by flash chomatography (silica, chloroform)

Sources & evidence

ORD record
ord-2a77e91c6c32445498e64bc6d139404f
Source dataset
uspto-grants-2009_08
Patent number
US07569516B2

Reaction notes

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