Water → HCID 178505704, compound

HRID 1090320Notes

Reaction equation

HRID 1090320 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:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:14]=1[CH2:15]Cl.O>C(O)C.CN(C=O)C>[Cl:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:14]=1[CH2:15][S:2][C:3]1[NH:4][C:5]2[CH:10]=[CH:9][N:8]=[CH:7][C:6]=2[N:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1086751-Chloro-2-(chloromethyl)-3-fluorobenzeneHCID 5360545SodiumHCID 178527813HCID 178527813, compound

Product 1

HCID 178505704HCID 178505704, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.34 g (0.015 g atom) of sodium in 70 mL of ethanol was added 2.0 g (0.013 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine. After stirring at room temperature for 25 minutes, the reaction mixture was evaporated to dryness in a rotary evaporator. To the residue was added 40 mL of DMF. To the resulting solution was added dropwise 2.33 g (0.013 mol) of 2-chloro-6-fluorobenzyl chloride in 3 mL of DMF. The reaction mixture was stirred overnight at room temperature and was then poured into 400 mL of chilled water. The precipitate that formed was collected by filtration and amounted to 3.11 g. An analytical sample (m.p. 224°-226° C.) was obtained by recrystallization from ethanol.

Workup

  1. customthe reaction mixture was evaporated to dryness in a rotary evaporator
  2. additionTo the residue was added 40 mL of DMF
  3. stirringThe reaction mixture was stirred overnight at room temperature
  4. customThe precipitate that formed
  5. filtrationwas collected by filtration
  6. customAn analytical sample (m.p. 224°-226° C.) was obtained by recrystallization from ethanol

Sources & evidence

ORD record
ord-2b56a1d7393141548d515ccbdfcd940b
Source dataset
uspto-grants-1992_01
Patent number
US05081253

Reaction notes

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