Water → HCID 15684608, compound

HRID 728163Notes

Reaction equation

HRID 728163 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]3[C:22]=2[CH3:23])=[CH:7][C:6]=1O)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])[O-].[K+].[K+]>S1(CCCC1)(=O)=O.C(OCC)(=O)C>[CH3:23][C:22]1[N:16]2[CH:17]=[CH:18][C:19]([CH3:21])=[CH:20][C:15]2=[N:14][C:13]=1[CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]2[N:4]=[C:1]([CH3:2])[O:3][C:10]=2[CH:9]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 15684669HCID 15684669, compound

Product 1

HCID 15684608HCID 15684608, compoundYield 28.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[2-(4-acetamido-3-hydroxyphenyl)-ethyl]-3,7-dimethylimidazo[1,2-a]pyridine (2.5 g) and phosphorus oxychloride (1.4 ml) in sulfolane (25 ml) was stirred for 1 hour at 100° C. The reaction mixture was added to a mixture of water and ethyl acetate and the separated aqueous layer was adjusted to pH 8 with potassium carbonate. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine and dried over magnesium sulfate. Evaporation of a solvent gave a residue, which was purified by a column chromatography on silica gel eluting with a mixture of chloroform and methanol (39:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo. The residue was crystallized from a mixture of ethyl acetate and diethyl ether to give 6-[2-(3,7-dimethylimidazo[1,2-a]pyridin-2-yl)ethyl]-2-methylbenzoxazole (0.67 g).

Workup

  1. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of a solvent
  5. customgave a residue, which
  6. customwas purified by a column chromatography on silica gel eluting with a mixture of chloroform and methanol (39:1, V/V)
  7. additionThe eluted fractions containing the desired product
  8. customwere collected
  9. customevaporated in vacuo
  10. customThe residue was crystallized from a mixture of ethyl acetate and diethyl ether

Sources & evidence

ORD record
ord-5e718d438a3a498184d8f38c651346b1
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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