Imidazole → HCID 131722283, compound

HRID 2300696Notes

Reaction equation

HRID 2300696 reaction equation
CS(OCCCCCCC1OC(N2C=CN=C2C)=NC=1C1C=CC([Cl:29])=CC=1)(=O)=[O:3].N1C=CN=C1.C(=O)([O-])[O-].[K+].[K+].[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[N:49]=[C:50]([N:64]3[CH:68]=[CH:67][N:66]=[C:65]3[CH3:69])[O:51][C:52]=2[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][N:59]2[CH:63]=[CH:62][N:61]=[CH:60]2)=[CH:44][CH:43]=1.[ClH:70].C(OCC)(=O)C>CO.O.CN(C)C=O>[OH2:3].[ClH:29].[ClH:41].[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[N:49]=[C:50]([N:64]3[CH:68]=[CH:67][N:66]=[C:65]3[CH3:69])[O:51][C:52]=2[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][N:59]2[CH:63]=[CH:62][N:61]=[CH:60]2)=[CH:44][CH:43]=1.[Cl:41][C:42]1[CH:47]=[CH:46][C:45]([C:48]2[N:49]=[C:50]([N:64]3[CH:68]=[CH:67][N:66]=[C:65]3[CH3:69])[O:51][C:52]=2[CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][N:59]2[CH:63]=[CH:62][N:61]=[CH:60]2)=[CH:44][CH:43]=1.[ClH:70].[ClH:29]

Participants

9

Reactant 5

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 18376451HCID 18376451, compoundHCID 18376480HCID 18376480, compoundHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 131722283HCID 131722283, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
92.5 °C

Procedure

A mixture of 6-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]hexyl methansulfonate(2.11 g), imidazole(660 mg), potassium carbonate(1.33 g) and N,N-dimethylformamide(40 ml) was stirred for 2 hours at 90-95° 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 evaporating 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-[6-(1-imidazolyl)hexyl]-2-(2-methyl-1-imidazolyl)oxazole(1.26 g, 64%). The oily substance (1.26 g) was dissolved in methanol(5 ml), and thereto a 4N-hydrochloric acid-ethyl acetate solution (1.7 ml) was added. The reaction mixture was concentrated. Ethyl acetate was added to the residue. The precipitated white powder was collected by filtration. This was recrystallized from methanol-acetone to give 4-(4-chlorophenyl)-5-[6-(1-imidazolyl)hexyl]-2-(2-methyl-1-imidazolyl)oxazole dihydrochloride hemihydrate(1.16 g, 49%). mp 171-173° 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 evaporating the solvent
  5. washFrom the fraction eluted with methanol-chloroform(3:97
  6. customv/v), obtained
  7. concentrationThe reaction mixture was concentrated
  8. additionEthyl acetate was added to the residue
  9. filtrationThe precipitated white powder was collected by filtration
  10. customThis was recrystallized from methanol-acetone

Sources & evidence

ORD record
ord-7c288770f43f403a86bc6432026ade63
Source dataset
uspto-grants-2002_12
Patent number
US06498179B1

Reaction notes

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