Dichloromethane → HCID 86589862, compound

HRID 1841217Notes

Reaction equation

HRID 1841217 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][NH:15][C:16](=O)[CH3:17])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1.C([O-])(O)=O.[Na+].C(Cl)Cl>COCCOC>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[CH:13]=[C:12]([CH2:14][NH:15][C:16](=[S:28])[CH3:17])[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 87949Lawesson's reagentHCID 516892Sodium BicarbonateHCID 69039095HCID 69039095, compound

Product 1

HCID 86589862HCID 86589862, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of N-[1-(3,4-dichloro-phenyl)-1H-imidazol-4-ylmethyl]-acetamide (1.1 g, 3.7 mmol) in 1,2 dimethoxyethane (11 ml) was added Lawesson's reagent (0.82 g, 2.0 mmol) and the mixture refluxed for 90 min. After addition of saturated NaHCO3 solution (50 ml) and extraction with CH2Cl2 (3×100 ml) the combined organic phases were dried (Na2SO4), concentrated and the obtained crude product was chromatographed [silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH=9:1)]. The title compound was obtained as a brown crystalline material (0.75 g, 68%). Mp. 166-170° C. (MeOH/CH2Cl2), MS: m/e=299 (M+).

Workup

  1. temperaturethe mixture refluxed for 90 min
  2. dry with materialwere dried (Na2SO4)
  3. concentrationconcentrated
  4. customthe obtained crude product
  5. customwas chromatographed
  6. wash[silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH=9:1)]

Sources & evidence

ORD record
ord-68ba02ef697046baaaa1d57abe1a4c70
Source dataset
uspto-grants-2004_01
Patent number
US06683097B2

Reaction notes

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