Acetic Acid → HCID 178473049, compound

HRID 636429Notes

Reaction equation

HRID 636429 reaction equation
[C:1](OCC)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:10][C:11]1[NH:15][N:14]=[C:13]([O:16][CH2:17][CH2:18][OH:19])[C:12]=1[S:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21].O.[C:30](O)(=[O:32])[CH3:31]>>[C:23]1([S:20]([C:12]2[C:13]([O:16][CH2:17][C:18]([O:32][CH2:30][CH3:31])=[O:19])=[N:14][N:15]3[C:1]([OH:6])=[CH:2][C:3]([CH3:5])=[N:10][C:11]=23)(=[O:21])=[O:22])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8868Ethyl AcetoacetateHCID 54398810HCID 54398810, compound

Product 1

HCID 178473049HCID 178473049, compoundYield 42%

Procedure

0.75 ml of ethyl acetoacetate was added to a solution of 1.14 g (4.9 mol) of 2-(5-amino-4-benzenesulphonyl-1H-pyrazol-3-yloxy)-ethanol in 10 ml of acetic acid and heated at reflux for 3 hrs. After cooling to RT the mixture was treated with 50 ml of H2O and extracted three times with CH2Cl2. The organic phases were dried (MgSO4), filtered and evaporated. Chromatography (SiO2, CH2Cl2/MeOH 19:1) of the residue yielded 0.8 g (42%) of ethyl 2-(3-benzenesulphonyl-7-hydroxy-5-methyl-pyrazolo[1,5-a]pyrimidin-2-yloxy)-acetate as a colorless oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hrs
  3. extractionextracted three times with CH2Cl2
  4. dry with materialThe organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-392506833b3e436a9fb3d7dcca72690c
Source dataset
uspto-grants-2001_02
Patent number
US06194410B1

Reaction notes

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