Hydrochloric Acid → 5-Amino-1-(2-fluorobenzyl)-3-(5-hydroxymethyl-2-furyl)-4-nitroso-pyrazole

HRID 1280434Notes

Reaction equation

HRID 1280434 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[C:4]([C:15]2[O:16][C:17]([CH2:20][OH:21])=[CH:18][CH:19]=2)[CH:3]=1.Cl.[N:23](OCC)=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])[N:5]=[C:4]([C:15]2[O:16][C:17]([CH2:20][OH:21])=[CH:18][CH:19]=2)[C:3]=1[N:23]=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8026Ethyl NitriteHCID 11430Potassium CarbonateHCID 120182115-Amino-1-(2-fluorobenzyl)-3-(5-hydroxymethyl-2-furyl)-pyrazole

Product 1

HCID 120182125-Amino-1-(2-fluorobenzyl)-3-(5-hydroxymethyl-2-furyl)-4-nitroso-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g (34.8 mmol) of 5-amino-1-(2-fluorobenzyl)-3-(5-hydroxymethyl-2-furyl)-pyrazole are initially introduced in a mixture of 66 ml of ethanol and 26.7 ml of 5% strength aqueous hydrochloric acid, treated in the course of 5 minutes with 26.4 ml of a 15% strength ethanolic solution of ethyl nitrite and stirred at room temperature for 1 h. The deep violet reaction solution is added to aqueous potassium carbonate solution and extracted with ethyl acetate. After evaporating the organic phase in vacuo, 8 g of the residue are obtained, which can be immediately reacted further. (Rf=0.17, T1E1, SiO2).

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter evaporating the organic phase in vacuo, 8 g of the residue
  3. customare obtained
  4. customwhich can be immediately reacted further

Sources & evidence

ORD record
ord-082017121fef4e0d8c80da402dbe545c
Source dataset
uspto-grants-2002_09
Patent number
US06451805B1

Reaction notes

Loading…