Nitric Acid → HCID 86751267, compound

HRID 1379581Notes

Reaction equation

HRID 1379581 reaction equation
[N+]([O-])(O)=O.N([O-])=O.[Na+].[OH:9][C:10]1([CH:23]=[CH:22][CH:21]=[CH:20][CH:19]1[C:24]([F:27])([F:26])[F:25])[CH2:11][C:12]1[N:13]([CH3:18])[C:14](S)=[N:15][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[OH:9][C:10]1([CH:23]=[CH:22][CH:21]=[CH:20][CH:19]1[C:24]([F:27])([F:26])[F:25])[CH2:11][C:12]1[N:13]([CH3:18])[CH:14]=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 10340Sodium CarbonateHCID 23668193Sodium Nitrite2×HCID 178480144HCID 178480144, compound

Product 1

HCID 86751267HCID 86751267, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a well stirred solution of nitric acid (8 ml) and water (8 ml) was added sodium nitrite (0.93 g). The reaction vessel was cooled externally with a water bath. 4-(1-hydroxy-2'-trifluoromethylbenzyl)-2-mercapto-3-methylimidazole (4.0 g) was added over 5 minutes to the greenish solution. After 1 hour, more sodium nitrite (3.0 g) was added and stirring was continued overnight. Sodium carbonate was added to saturate the mixture. Ethyl acetate was added to dissolve all organic solids. The remaining solid was removed by filtration. Water was added to the filtrate. The layers were separated after being shaken. Removal of water under reduced pressure gave 4-(1-hydroxy-2'-trifluoromethylbenzyl)-3-methylimidazole (2.8 g).

Workup

  1. temperatureThe reaction vessel was cooled externally with a water bath
  2. waitwas continued overnight
  3. concentrationto saturate the mixture
  4. additionEthyl acetate was added
  5. dissolutionto dissolve all organic solids
  6. customThe remaining solid was removed by filtration
  7. additionWater was added to the filtrate
  8. customThe layers were separated
  9. stirringafter being shaken
  10. customRemoval of water under reduced pressure

Sources & evidence

ORD record
ord-7b46ccdb218c45908a292d14a3b280de
Source dataset
uspto-grants-1997_09
Patent number
US05672567

Reaction notes

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