Water → HCID 68515521, compound

HRID 1716616Notes

Reaction equation

HRID 1716616 reaction equation
Br[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[N+:21]([O-:23])=[O:22].[CH3:24][NH2:25].O>C(OCC)(=O)C>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:12]([Cl:13])[C:7]=1[N:6]1[C:2]([NH:25][CH3:24])=[C:3]([N+:21]([O-:23])=[O:22])[C:4]([C:19]#[N:20])=[N:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 6329MethylamineHCID 22618615HCID 22618615, compound

Product 1

HCID 68515521HCID 68515521, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 5-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitro-1H-pyrazole-3-carbonitrile (EP 295118 A1, 50 mg, 0.12 mmol) and methylamine (2M in tetrahydrofuran, 1.0 mmol, 2.0 mmol) was heated at 55° C. for 2.5 h. To the reaction mixture was added water (5 ml), followed by ethyl acetate (5 ml). The two layers were separated and the aqueous layer was extracted with ethyl acetate (3×5 ml). The combined organic phases were dried (MgSO4) and concentrated in vacuo to give the titled compound (42 mg).

Workup

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (3×5 ml)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d945d46b1a74f199850324415882718
Source dataset
uspto-grants-2010_09
Patent number
US07803832B2

Reaction notes

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