Potassium Carbonate → HCID 9993129, compound

HRID 728135Notes

Reaction equation

HRID 728135 reaction equation
[CH2:1]([NH:3][C:4](=[O:21])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)=[CH:8][C:7]=1O)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.O1CCCC1.O>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][CH2:12][C:9]1[CH:10]=[CH:11][C:6]2[N:5]=[C:4]([NH:3][CH2:1][CH3:2])[O:21][C:7]=2[CH:8]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 10424066HCID 10424066, compound

Product 1

HCID 9993129HCID 9993129, compoundYield 16.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[2-{4-(3-ethylureido)-3-hydroxyphenyl}ethyl]pyridine (3.3 g) and polyphosphate ester (30 g) was stirred at 90° to 100° C. for 1.5 hours. The reaction mixture was dissolved in a mixture of ethyl acetate, tetrahydrofuran and water and the resultant solution was adjusted to pH 8 with potassium carbonate. The separated organic layer was washed with brine and dried over magnesium sulfate. The crude product obtained by concentration was purified by silica gel column chromatography eluting with a solution of chloroform and methanol (39:1 V/V). The eluted fractions containing desired product were evaporated to give 6-[2-(2-pyridyl)ethyl]-2-ethylaminobenzoxazole (0.5 g).

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customThe crude product obtained by concentration
  4. customwas purified by silica gel column chromatography
  5. washeluting with a solution of chloroform and methanol (39:1 V/V)
  6. additionThe eluted fractions containing desired product
  7. customwere evaporated

Sources & evidence

ORD record
ord-ebc2a704ec104f31ac2290a18983debf
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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