Chlorosuccinimide → HCID 66986175, compound

HRID 1254037Notes

Reaction equation

HRID 1254037 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[N:4]=[CH:3]1.C1C(=O)N([Cl:22])C(=O)C1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[Cl:22][C:6]1[N:2]([CH3:1])[CH:3]=[N:4][C:5]=1[C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 59598059HCID 59598059, compound

Product 1

HCID 66986175HCID 66986175, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
50 °C

Procedure

To 4-(1-methyl-1H-imidazol-4-yl)benzonitrile (Step 2, 1.05 g, 5.73 mmol) in methylene chloride (15 mL) was added NCS (765 mg, 5.73 mmol) and 3 drops of TFA. After stirring at 50° C. for 3 hrs, the reaction was diluted with 20 mL of methylene chloride and quenched with aq NaHCO3. The organic layer was washed with water, brine, dried over MgSO4, filtered, and concentrated to give 4-(5-chloro-1-methyl-1H-imidazol-4-yl)benzonitrile. LCMS: [M+1]=218.

Workup

  1. customquenched with aq NaHCO3
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-488b9bd0bb0543cfb263ecb569f8c7ae
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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