Sodium Carbonate → HCID 22618561, compound

HRID 1078466Notes

Reaction equation

HRID 1078466 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]([F:22])([F:21])[F:20])[CH:3]=1.[S-:23][C:24]#[N:25].[K+].BrBr.C(=O)([O-])[O-].[Na+].[Na+]>CO>[NH2:1][C:2]1[N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:15])([F:16])[F:17])=[CH:11][C:12]=2[Cl:13])[N:5]=[C:4]([C:19]([F:22])([F:21])[F:20])[C:3]=1[S:23][C:24]#[N:25]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 516872Potassium thiocyanateHCID 22618376HCID 22618376, compound

Product 1

HCID 22618561HCID 22618561, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A stirred mixture of 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole (0.7 g) and potassium thiocyanate (0.55 g) in methanol (15 ml) was treated with a solution of bromine (0.3 g) in methanol (2 ml) at 0°-5° C. Stirring was maintained at this temperature for 1.5 hours, and the mixture was poured onto ice water, and brought to pH 9 by the addition of sodium carbonate. The product was filtered, washed with water and dried. Purification by chromatography on silica (Merck 230-400 mesh, 0.7 kg cm-2) eluting with dichloromethane gave 5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-thiocyanato-3-trifluoromethylpyrazole, in the form of a white solid, m.p. 49°-50° C.

Workup

  1. temperaturewas maintained at this temperature for 1.5 hours
  2. additionthe mixture was poured onto ice water
  3. filtrationThe product was filtered
  4. washwashed with water
  5. customdried
  6. customPurification by chromatography on silica (Merck 230-400 mesh, 0.7 kg cm-2)
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-7323ba40946c4e74955de31b0c01f88d
Source dataset
uspto-grants-1996_08
Patent number
US05547974

Reaction notes

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