Ethyl Bromide → HCID 22618612, compound

HRID 861257Notes

Reaction equation

HRID 861257 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[Mg].C(Br)C.[NH2:9][C:10]1[N:14]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:25])([F:24])[F:23])=[CH:17][C:16]=2[Cl:26])[N:13]=[C:12]([C:27]([F:30])([F:29])[F:28])[C:11]=1[S:31]C#N>C(OCC)C.O>[NH2:9][C:10]1[N:14]([C:15]2[C:20]([Cl:21])=[CH:19][C:18]([C:22]([F:23])([F:24])[F:25])=[CH:17][C:16]=2[Cl:26])[N:13]=[C:12]([C:27]([F:28])([F:30])[F:29])[C:11]=1[S:31][CH2:1][CH3:2]

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 5462224MagnesiumHCID 22618561HCID 22618561, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 22618612HCID 22618612, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of ethyl magnesium bromide, prepared from magnesium (0.57 g) and ethyl bromide (2.6 g) in dry diethyl ether (25 ml), was added dropwise to a stirred solution of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-thiocyanato-3-trifluoromethylpyrazole (5.0 g) in dry ether (50 ml) at -20° C. After stirring for a further 2 hours at room temperature, water (130 ml) was carefully added, and stirring maintained for 0.25 hour. The ether layer was separated, dried over anhydrous magnesium sulphate, and evaporated in vacuo to give a yellow gum. Purification by chromatography on silica (Merck, 200-400 mesh, 0.7 kg cm-2) eluting with dichloromethane-petroleum ether (1:1) gave a product, which recrystallized from hexane to furnish 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethylthio-3-trifluoromethylpyrazole, in the form of white needles, m.p. 116°-116.5° C.

Workup

  1. stirringstirring
  2. temperaturemaintained for 0.25 hour
  3. customThe ether layer was separated
  4. dry with materialdried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customto give a yellow gum
  7. customPurification by chromatography on silica (Merck, 200-400 mesh, 0.7 kg cm-2)
  8. washeluting with dichloromethane-petroleum ether (1:1)
  9. customgave a product, which
  10. customrecrystallized from hexane

Sources & evidence

ORD record
ord-786e5b9010924123b7b7ca90990730ec
Source dataset
uspto-grants-1998_02
Patent number
US05714191

Reaction notes

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