Imidazole → HCID 53894648, compound

HRID 1195817Notes

Reaction equation

HRID 1195817 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.C(N(CC)CC)C.[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([Cl:23])[N:22]=1)[C:17](Cl)=[O:18].Cl.C(N(CC)CC)C>O1CCCC1>[Cl:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([Cl:23])[N:22]=1)[C:17]([N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)=[O:18]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 11130Triethylamine hydrochlorideHCID 27816432,6-Dichloro-isonicotinoyl chloride

Product 1

HCID 53894648HCID 53894648, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.8 g (0.10 mole) of imidazole and 15.3 ml (0.11 mole) of triethylamine are stirred in 100 ml of tetrahydrofuran. While cooling at 25°-30° C., a solution of 23.1 g (0.11 mole) of 2,6-dichloroisonicotinic acid chloride in 20 ml of tetrahydrofuran is then added dropwise, triethylamine hydrochloride separating. This is filtered off with suction and the filtrate is concentrated to 26.4 g of crude product. Recrystallisation from ethyl acetate yields 20.1 g (83% of the theoretical amount) of pure substance; m.p. 148°-151° C.

Workup

  1. temperatureWhile cooling at 25°-30° C.
  2. filtrationThis is filtered off with suction
  3. concentrationthe filtrate is concentrated to 26.4 g of crude product
  4. customRecrystallisation from ethyl acetate
  5. customyields 20.1 g (83% of the theoretical amount) of pure substance

Sources & evidence

ORD record
ord-671637b9cda14346a38ad50e4a8afcca
Source dataset
uspto-grants-1992_05
Patent number
US05112840

Reaction notes

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