Sulfuric Acid → HCID 15028917, compound

HRID 2099043Notes

Reaction equation

HRID 2099043 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([O:18][CH2:19][CH3:20])=[C:16]([S:21][C:22]([F:25])([F:24])[F:23])[C:15]([C:26]#[N:27])=[N:14]1.S(=O)(=O)(O)[OH:29]>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([O:18][CH2:19][CH3:20])=[C:16]([S:21][C:22]([F:25])([F:23])[F:24])[C:15]([C:26]([NH2:27])=[O:29])=[N:14]1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 15017021HCID 15017021, compound

Product 1

HCID 15028917HCID 15028917, compoundYield 73%

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 1-(2,6-dichloro-4-trifluoromethylpheny)-5-ethoxy-4-trifluoromethylthio-1 H-pyrazole-3-carbonitrile (0.55 g, 1.22 mmol) and concentrated sulfuric acid (0.55 ml) was heated at 100° C. for 3 hours. The cooled mixture was added to ice water and the precipitate filtered off, washed with water and air-dried. The crude product was dissolved in heptanes/ethyl acetate (1:1) and filtered. The filtrate was evaporated to give the title compound (0.42 g, yield 73%) as yellowish crystals, mp 161° C., 1H NMR (CDCl3): 1.32 (t, 3H, CH3), 4.68 (q, 2H, OCH2), 5.54 and 6.69 (bs, 2H, C(O)NH2), and 7.77 (s, 2H, Ar—H).

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed with water
  3. customair-dried
  4. dissolutionThe crude product was dissolved in heptanes/ethyl acetate (1:1)
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-83a9e1f9c1fd47a69643e42b59cc521f
Source dataset
uspto-grants-2009_08
Patent number
US07569516B2

Reaction notes

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