Hydrochloric Acid → HCID 19823298, compound

HRID 728134Notes

Reaction equation

HRID 728134 reaction equation
[CH2:1]([NH:3][C:4](=[O:21])[NH:5][C:6]1[CH:7]=[C:8]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:9]=[CH:10][C:11]=1O)[CH3:2].C(OCC)(=O)C.[ClH:28].C(=O)([O-])[O-].[K+].[K+]>O>[ClH:28].[ClH:28].[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][CH2:13][C:8]1[CH:9]=[CH:10][C:11]2[O:21][C:4]([NH:3][CH2:1][CH3:2])=[N:5][C:6]=2[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 15171497HCID 15171497, compound

Product 1

HCID 19823298HCID 19823298, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-[2-{3-(3-ethylureido)-4-hydroxyphenyl}ethyl]pyridine (3.3 g) and polyphosphate ester (30 g) was stirred at 110° to 115° C. for one hour. To a reaction mixture was added a mixture of ethyl acetate and water and the resultant mixture was acidified to pH 1.0 with 10% hydrochloric acid. The separated aqueous layer was adjusted to pH 8.0 with aqueous 20% potassium carbonate and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was subjected to column chromatography on silica gel. The fraction eluted with a mixture of chloroform and methanol (19:1 V/V) was collected and the solvent was evaporated in vacuo. The oily residue was crystallized from 15% hydrogen chloride-ethanol and tetrahydrofuran to give 5-[2-(2-pyridyl)ethyl]-2-ethylaminobenzoxazole dihydrochloride (0.97 g).

Workup

  1. additionTo a reaction mixture was added
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated in vacuo
  6. washThe fraction eluted with a mixture of chloroform and methanol (19:1 V/V)
  7. customwas collected
  8. customthe solvent was evaporated in vacuo
  9. customThe oily residue was crystallized from 15% hydrogen chloride-ethanol and tetrahydrofuran

Sources & evidence

ORD record
ord-25f02d56d0c842d0923961a8d4ea2229
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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