Water → HCID 178420433, compound

HRID 1090322Notes

Reaction equation

HRID 1090322 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.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>CO>[C:13]1([CH2:12][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:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7503Benzyl ChlorideHCID 5360545SodiumHCID 178527813HCID 178527813, compound

Product 1

HCID 178420433HCID 178420433, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.26 g (0.055 g atom) of sodium in 300 mL of methanol was added 7.56 g (0.05 mol) of 2-mercapto-1H-imidazo[4,5-c]pyridine with stirring. After 20 minutes, the reaction mixture was evaporated to dryness in a rotary evaporator. Dimethyl formamide (200 mL) was added to the residue. To the resulting solution was added dropwise 6.33 g (0.05 mol) of benzylchloride. The reaction mixture was stirred for 5 hours at room temperature and was then poured into 1500 mL of water. The product was removed by filtration and amounted to 9.5 g, m.p. 175°-177° C. The product was triturated with hot ethyl acetate and refiltered. The product amounted to 8.11 g, m.p. 175°-177° C. A portion recrystallized from ethyl acetate gave the analytical sample (m.p. 175°-177° C.).

Workup

  1. customthe reaction mixture was evaporated to dryness in a rotary evaporator
  2. additionDimethyl formamide (200 mL) was added to the residue
  3. stirringThe reaction mixture was stirred for 5 hours at room temperature
  4. customThe product was removed by filtration
  5. customThe product was triturated with hot ethyl acetate
  6. customA portion recrystallized from ethyl acetate
  7. customgave the analytical sample (m.p. 175°-177° C.)

Sources & evidence

ORD record
ord-cc6cdd0e2aad416e82fa142e5581c402
Source dataset
uspto-grants-1992_01
Patent number
US05081253

Reaction notes

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