Sodium borohydride → HCID 10294562, compound

HRID 2253779Notes

Reaction equation

HRID 2253779 reaction equation
[C:1]([C:3]1[C:4]([C:25]([F:28])([F:27])[F:26])=[N:5][N:6]([C:13]2[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][C:14]=2[Cl:24])[C:7]=1[N:8]=[CH:9]OCC)#[N:2].[BH4-].[Na+]>CO>[C:1]([C:3]1[C:4]([C:25]([F:27])([F:28])[F:26])=[N:5][N:6]([C:13]2[C:14]([Cl:24])=[CH:15][C:16]([C:20]([F:22])([F:21])[F:23])=[CH:17][C:18]=2[Cl:19])[C:7]=1[NH:8][CH3:9])#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 53786085HCID 53786085, compound

Product 1

HCID 10294562HCID 10294562, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethyleneamino-3-trifluoromethylpyrazole (1.0 g) in methanol (10 ml) stirred at room temperature was added sodium borohydride (0.17 g). After 2 hours an additional 0.17 g of sodium borohydride was added, and another 0.34 g added after 1 hours. One hour later the mixture was poured onto water (80 ml). The combined extracts were dried over anhydrous magnesium sulphate, filtered, and evaporated in vacuo. The white solid thus obtained was purified by chromatography on silica (Merck, 230-400 mesh, 0.7 kg cm-2) with dichloromethane as eluent, to furnish 4-cyano-5-methylamino-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-trifluoromethylpyrazole as a white solid (0.6 g), m.p. 200°-202° C.

Workup

  1. additionanother 0.34 g added after 1 hours
  2. additionOne hour later the mixture was poured onto water (80 ml)
  3. dry with materialThe combined extracts were dried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe white solid thus obtained
  7. customwas purified by chromatography on silica (Merck, 230-400 mesh, 0.7 kg cm-2) with dichloromethane as eluent

Sources & evidence

ORD record
ord-7a6e6ea1a5224bcf8d75598f69b7513f
Source dataset
uspto-grants-1993_08
Patent number
US05232940

Reaction notes

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