Imidazole → HCID 70201480, compound

HRID 342455Notes

Reaction equation

HRID 342455 reaction equation
[Cl:1][CH2:2][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14](=[O:23])[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[C:5]=2[O:6][C:7]=1[CH3:8].[NH:24]1[CH:28]=[CH:27][N:26]=[CH:25]1.C(N(CC)CC)C>ClCCCl>[ClH:1].[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:22])[C:15]=1[C:14]([NH:13][C:9]1[C:5]2[O:6][C:7]([CH3:8])=[C:3]([CH2:2][N:24]3[CH:28]=[CH:27][N:26]=[CH:25]3)[C:4]=2[CH:12]=[CH:11][CH:10]=1)=[O:23]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 8471TriethylamineHCID 70200093HCID 70200093, compound

Product 1

HCID 70201480HCID 70201480, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 3-chloromethyl-7-(2,6-dichlorobenzoylamino)-2-methylbenzo[b]furan (150 mg), imidazole (33 mg) and triethylamine (62 mg) in 1,2-dichloroethane (1.5 ml) was refluxed for 3 hours. The reaction mixture was evaporated in vacuo and the residue was purified by column chromatography on silica gel. The obtained oil was crystallized from a mixture of ethyl acetate and diisopropyl ether and the crystalline was treated with ethanolic hydrogen chloride. The separated solid was collected and washed with ethanol to give 7-(2,6-dichlorobenzoylamino)-3-(imidazol-1-yl)methyl-2-methylbenzo[b]furan hydrochloride (62 mg).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe residue was purified by column chromatography on silica gel
  4. customThe obtained oil was crystallized from a mixture of ethyl acetate and diisopropyl ether
  5. additionthe crystalline was treated with ethanolic hydrogen chloride
  6. customThe separated solid was collected
  7. washwashed with ethanol

Sources & evidence

ORD record
ord-75ba9ae5f5f1441cae3d42b107ccfe05
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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