3-(Trifluoromethyl)benzyl chloride → HCID 178506164, compound

HRID 1090318Notes

Reaction equation

HRID 1090318 reaction equation
[Na].[SH:2][C:3]1[NH:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:11]=1.Cl[CH2:13][C:14]1[CH:15]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:18][CH:19]=1>CO.CN(C=O)C>[F:21][C:20]([F:22])([F:23])[C:16]1[CH:15]=[C:14]([CH2:13][S:2][C:3]2[NH:4][C:5]3[CH:10]=[CH:9][N:8]=[CH:7][C:6]=3[N:11]=2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 697163-(Trifluoromethyl)benzyl chlorideHCID 5360545SodiumHCID 178527813HCID 178527813, compound

Product 1

HCID 178506164HCID 178506164, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.15 g (0.0065 g atom) of sodium in 35 mL of methanol was added 1.0 g (0.0066 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. After stirring for 15 minutes at room temperature, the methanol was removed in a rotary evaporator. The residue was dissolved in 20 mL of DMF and 1.28 g (0.0066 mol) of α'-chloro-α,α,α-trifluoro-m-xylene in 2 mL of DMF was added dropwise to the reaction solution. The reaction mixture was stirred at room temperature overnight and was then poured into 150 mL of ice water. The product which crystallized was collected and amounted to 1.61 g. An analytical sample (m.p. 148°-150° C.) was obtained by recrystallization from acetonitrile.

Workup

  1. customthe methanol was removed in a rotary evaporator
  2. dissolutionThe residue was dissolved in 20 mL of DMF
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. customThe product which crystallized
  5. customwas collected
  6. customAn analytical sample (m.p. 148°-150° C.) was obtained by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-b58604d9a94d4ca5a075bda3fcbcee19
Source dataset
uspto-grants-1992_01
Patent number
US05081253

Reaction notes

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