Sodium Carbonate → HCID 22618561, compound

HRID 1416844Notes

Reaction equation

HRID 1416844 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-52d4a161a717418a83a96c8ce09f1f18
Source dataset
uspto-grants-1999_06
Patent number
US05916618

Reaction notes

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