Sodium borohydride → HCID 22418310, compound

HRID 1720459Notes

Reaction equation

HRID 1720459 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([Cl:18])=[C:16]([C:19]#[N:20])[C:15]([S:21][C:22]([F:25])([F:24])[F:23])=[C:14]1[CH:26]=[CH:27][C:28]#[N:29].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([Cl:12])[C:3]=1[N:13]1[C:17]([Cl:18])=[C:16]([C:19]#[N:20])[C:15]([S:21][C:22]([F:25])([F:24])[F:23])=[C:14]1[CH2:26][CH2:27][C:28]#[N:29]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 54334327HCID 54334327, compound

Product 1

HCID 22418310HCID 22418310, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 3.03 g (6.18 mmoles) portion of the 1-(2,6-dichloro-4-trifluoromethylphenyl)-2-(2-cyanoethenyl)-3-trifluoromethylthio-4-cyano-5-chloropyrrole prepared above was treated with 467 mg (12.4 mmoles) of sodium borohydride in 250 mL of ethanol at room temperature for 16 hours. An additional 234 mg (6.18 mmoles) of sodium borohydride was then added in two equal portions over a two hour period to complete the reaction. The solvent was then removed under reduced pressure and the residue poured into 25 mL of ice water. The mixture was acidified with aqueous 6N HCl, extracted with dichloromethane (2×50 mL) and the organic extracts were partitioned with saturated aqueous NaHCO3 solution, dried over anhydrous MgSO4 and concentrated. The residue was chromatographed on silica gel eluting with 70/30 v/v dichloromethane-hexane to furnish 1.52 g (50%) of 1-(2,6-dichloro-4-trifluoromethylphenyl)-2-(2-cyanoethyl)-3-trifluoromethylthio-4-cyano-5-chloropyrrole (ASE 196) as a white solid of melting point 150° C.

Workup

  1. customthe reaction
  2. customThe solvent was then removed under reduced pressure
  3. additionthe residue poured into 25 mL of ice water
  4. extractionextracted with dichloromethane (2×50 mL)
  5. customthe organic extracts were partitioned with saturated aqueous NaHCO3 solution
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was chromatographed on silica gel eluting with 70/30 v/v dichloromethane-hexane

Sources & evidence

ORD record
ord-d4caac17244d457f99de1bec9f1203ed
Source dataset
uspto-grants-1996_04
Patent number
US05506260

Reaction notes

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