Sodium Hydroxide → HCID 86597885, compound

HRID 459631Notes

Reaction equation

HRID 459631 reaction equation
S([O:5][CH2:6][CH2:7][N:8]1[C:12]([NH2:13])=[C:11]([NH2:14])[CH:10]=[N:9]1)(O)(=O)=O.[OH-].[Na+].Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19]>O.O1CCOCC1>[NH2:13][C:12]1[N:8]([CH2:7][CH2:6][OH:5])[N:9]=[CH:10][C:11]=1[NH:14][C:18](=[O:19])[O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 874816672-(4,5-Diamino-1H-pyrazol-1-YL)ethanol sulfate

Product 1

HCID 86597885HCID 86597885, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-(4,5-diamino-1H-pyrazol-1-yl)ethanol sulfate (5 g) in water (30 ml) and dioxane (15 ml) was added aqueous sodium hydroxide solution under ice-cooling to adjust the mixture to pH 7. Phenyl chloroformate (3.42 g) was added to the mixture with controlling pH at 7, and the whole mixture was stirred at room temperature for 2 hours. The reaction mixture was extracted with ethyl acetate-tetrahydrofuran (1:1) and the extract was dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a crude product of phenyl [5-amino-1-(2-hydroxyethyl)-1H-pyrazol-4-yl]carbamate as an oil, which was used for Preparation 44 without further purification.

Workup

  1. temperaturecooling
  2. extractionThe reaction mixture was extracted with ethyl acetate-tetrahydrofuran (1:1)
  3. dry with materialthe extract was dried over anhydrous magnesium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-8f0d272d5ab54d828853135bfffb66dc
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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