Sulfuric Acid → HCID 18950668, compound

HRID 1492559Notes

Reaction equation

HRID 1492559 reaction equation
C([NH:3][CH:4]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:5][CH2:6][C:7]1[CH:19]=[CH:18][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=1)=O.S(=O)(=O)(O)O>C(O)C.O1CCCC1.O>[NH2:3][CH:4]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=1

Participants

6

Reactant 2

HCID 1118Sulfuric AcidHCID 18950739HCID 18950739, compound

Product 1

HCID 18950668HCID 18950668, compoundYield 36.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

In a mixed solvent of 4 ml of ethanol, 4 ml of tetrahydrofuran, and 4 ml of water was dissolved 150 mg of ethyl 4-[3-formamido-3-(3-pyridyl)propyl]phenoxyacetate, followed by addition of 0.15 ml of conc. sulfuric acid, which was then heated to 60° C. and stirred for 12 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, followed by addition of methanol-methylene chloride (5:95 v/v) and water. While stirring, the property of the solution was adjusted to weak alkalinity with gradual addition of saturated aqueous sodium hydrogencarbonate solution. After separation of the organic phase, which was then extracted with methanol-methylene chloride (5:95 v/v) from the aqueous phase and washed in saturated aqueous sodium chloride followed by drying over magnesium sulfate and distillation of the solvent, 50 mg of ethyl 4-[3-amino-3-(3-pyridyl)propyl]phenoxyacetate was obtained.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionfollowed by addition of methanol-methylene chloride (5:95 v/v) and water
  4. stirringWhile stirring
  5. additionthe property of the solution was adjusted to weak alkalinity with gradual addition of saturated aqueous sodium hydrogencarbonate solution
  6. customAfter separation of the organic phase, which
  7. extractionwas then extracted with methanol-methylene chloride (5:95 v/v) from the aqueous phase
  8. washwashed in saturated aqueous sodium chloride
  9. dry with materialby drying over magnesium sulfate and distillation of the solvent

Sources & evidence

ORD record
ord-1569ee107700406ab5988a6c3d1a52c3
Source dataset
uspto-grants-1994_12
Patent number
US05374641

Reaction notes

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