Imidazole → 1-(N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl)imidazole

HRID 1248930Notes

Reaction equation

HRID 1248930 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Cl:20])[C:5]2[O:9][CH:8]([CH2:10][N:11]([CH2:15][CH2:16][CH2:17][CH3:18])[C:12](Cl)=[O:13])[CH2:7][C:6]=2[CH:19]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([Cl:20])[C:5]2[O:9][CH:8]([CH2:10][N:11]([CH2:15][CH2:16][CH2:17][CH3:18])[C:12]([N:21]3[CH:25]=[CH:24][N:23]=[CH:22]3)=[O:13])[CH2:7][C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 13563317N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl chloride

Product 1

HCID 135633181-(N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl)imidazoleYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

13.5 g (0.04 mole) of N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl chloride were added dropwise to a solution of 6.8 g (0.1 mole) of imidazole in 150 ml of dry tetrahydrofuran at 20° C. The mixture was stirred for 6 hours at 70° C., after which it was cooled to 20° C., and the resulting precipitate was filtered off under suction. The filtrate was evaporated down under reduced pressure, the residue was dissolved in 200 ml of methylene chloride, the solution was washed with three times 80 ml of water, dried and evaporated down, the resin which remained was left to stand for 3 hours at 0° C. with 30 ml of diethyl ether, and the crystals formed were filtered off under suction. 12.8 g of 1-(N-(5,7-dichloro-2,3-dihydrobenzofuran-2-ylmethyl)-N-butylcarbamyl)imidazole of melting point 98°-100° C. were obtained (compound No. 1).

Workup

  1. temperatureafter which it was cooled to 20° C.
  2. filtrationthe resulting precipitate was filtered off under suction
  3. customThe filtrate was evaporated down under reduced pressure
  4. dissolutionthe residue was dissolved in 200 ml of methylene chloride
  5. washthe solution was washed with three times 80 ml of water
  6. customdried
  7. customevaporated down
  8. waitthe resin which remained was left
  9. waitto stand for 3 hours at 0° C. with 30 ml of diethyl ether
  10. customthe crystals formed
  11. filtrationwere filtered off under suction

Sources & evidence

ORD record
ord-1ef20224cc7746b39b3f857a1fecebcc
Source dataset
uspto-grants-1986_12
Patent number
US04628058

Reaction notes

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