Imidazole → HCID 86756284, compound

HRID 2300695Notes

Reaction equation

HRID 2300695 reaction equation
CS(OCCCCCC1OC(N2C=CN=C2C)=NC=1C1C=CC([Cl:28])=CC=1)(=O)=[O:3].N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+].[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[N:48]=[C:49]([N:62]3[CH:66]=[CH:65][N:64]=[C:63]3[CH3:67])[O:50][C:51]=2[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][N:57]2[CH:61]=[CH:60][N:59]=[CH:58]2)=[CH:43][CH:42]=1.Cl.C(OCC)(=O)C>CO.C(OCC)(=O)C.O.CN(C)C=O>[OH2:3].[ClH:28].[ClH:40].[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C:47]2[N:48]=[C:49]([N:62]3[CH:66]=[CH:65][N:64]=[C:63]3[CH3:67])[O:50][C:51]=2[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][N:57]2[CH:61]=[CH:60][N:59]=[CH:58]2)=[CH:43][CH:42]=1

Participants

10

Reactant 5

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 18376469HCID 18376469, compoundHCID 18376490HCID 18376490, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 86756284HCID 86756284, compoundYield 164.9%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]pentyl methanesulfonate(2.20 g), imidazole(710 mg), potassium carbonate(1.43 g) and N,N-dimethylformamide(40 ml) was stirred for 3 hours at 80-90° C. Water was added to the reaction mixture. The resulting mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, and dried(MgSO4). The residue obtained by evaporated the solvent was subjected to silica gel column chromatography. From the fraction eluted with methanol-chloroform(3:97, v/v), obtained was 4-(4-chlorophenyl)-5-[5-(1-imidazolyl)pentyl]-2-(2-methyl-1-imidazolyl)oxazole(1.45 g, 71%). The oily substance(1.45 g) was dissolved in methanol(6 ml), and thereto a 4N-hydrochloric acid-ethyl acetate solution (2 ml) was added. Ethyl acetate was then added to the reaction mixture. The precipitated white powder was collected by filtration, and washed with ethyl acetate-acetone to give 4-(4-chlorophenyl)-5-[5-(1-imidazolyl)pentyl]-2-(2-methyl-1-imidazolyl)oxazole dihydrochloride monohydrate(1.47 g, 58%). mp 197-199° C.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water, and dried(MgSO4)
  3. customThe residue obtained
  4. customby evaporated the solvent
  5. washFrom the fraction eluted with methanol-chloroform(3:97
  6. customv/v), obtained
  7. filtrationThe precipitated white powder was collected by filtration
  8. washwashed with ethyl acetate-acetone

Sources & evidence

ORD record
ord-a8af5b0fbcca4b58ba51ba264c45ddce
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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