Imidazole → HCID 19965983, compound

HRID 977815Notes

Reaction equation

HRID 977815 reaction equation
S(O[CH2:6][CH2:7][CH2:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([S:17][CH3:18])[C:12]=1[NH:19][C:20](=[O:36])[CH2:21][CH:22]1[C:35]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:29][C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2)(C)(=O)=O.[NH:37]1[CH:41]=[CH:40][N:39]=[CH:38]1>CN(C)C=O.C(OCC)(=O)C>[N:37]1([CH2:6][CH2:7][CH2:8][O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17][CH3:18])[C:12]=2[NH:19][C:20](=[O:36])[CH2:21][CH:22]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:28]=3[O:29][C:30]3[C:35]2=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:41]=[CH:40][N:39]=[CH:38]1

Participants

5

Reactant 2

HCID 795ImidazoleHCID 19966016HCID 19966016, compound

Product 1

HCID 19965983HCID 19965983, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

251 mg of the crude crystals of N-{2-[3-(mesyloxy)propoxy]methyl-6-methylthiophenyl}-2-(9H-xanthen-9-yl)acetamide [prepared as described in step (i) above] were suspended in 3 ml of dimethylformamide. 162 mg (2.39 mmol) of imidazole were added to the suspension, and the mixture was stirred for 5.5 hours at 90° C. At the end of this time, the reaction mixture was allowed to return to room temperature, after which it was diluted with ethyl acetate and washed several times with water. The solvent was then removed by distillation under reduced pressure, and the resulting residue was subjected to column chromatography through 15 g of silica gel. Fractions eluted with mixtures of methylene chloride and methanol ranging from 100:2 to 100:7 by volume were collected. Recrystallization from a mixture of methylene chloride and methanol afforded 162 mg (yield 68%) of the title compound as crystals, melting at 176.5°-177° C.

Workup

  1. customto return to room temperature
  2. washwashed several times with water
  3. customThe solvent was then removed by distillation under reduced pressure
  4. washFractions eluted with mixtures of methylene chloride and methanol ranging from 100:2 to 100:7 by volume
  5. customwere collected
  6. customRecrystallization
  7. additionfrom a mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-7652913b21ac4b43863f71b78c6d47da
Source dataset
uspto-grants-1997_03
Patent number
US05614550

Reaction notes

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