Sulfuric Acid → HCID 178526541, compound

HRID 2065792Notes

Reaction equation

HRID 2065792 reaction equation
[CH:1]1([C:4]2[NH:5][C:6]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[C:7]([C:9]3[N:14]=[C:13](N)[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1.[OH:27]S(O)(=O)=O.N([O-])=O.[Na+].OP([O-])(O)=O.[Na+].[OH-].[Na+]>CS(C)=O.O>[CH:1]1([C:4]2[NH:5][C:6]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])=[C:7]([C:9]3[N:14]=[C:13]([OH:27])[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 23672064Monosodium phosphateHCID 178508318HCID 178508318, compound

Product 1

HCID 178526541HCID 178526541, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

6-[2-Cyclopropyl-5-(2,4-difluorophenyl)-1H-imidazol-4-yl]-3-nitro-pyridin-2-amine (5.51 g, 15.41 mmol) is suspended in dimethyl sulfoxide (DMSO, 32 mL), water (25 mL), and concentrated H2SO4 (6 mL). The suspension is cooled at 0° C. and sodium nitrite (2.13 g, 30.81 mmol) is added portionwise at such a rate that the temperature is maintained below 5° C. The mixture is stirred at 0° C. for 30 min, and then is allowed to warm to RT, and is stirred until liquid chromatography/mass spectrometry (LC/MS) shows complete conversion of the starting material (1 hour). A 0.8 M aqueous solution of sodium phosphate monobasic (200 mL) is added to the mixture. A yellow suspension is formed. Aqueous 1 N NaOH is then added until the pH rises to 8. The mixture is stirred for 30 h, filtered, and the solid is rinsed with water, and then dried under reduced pressure to afford the title compound (4.53 g, 82%). LC-ES/MS m/z 358.9 (M+1).

Workup

  1. temperatureis maintained below 5° C
  2. temperatureto warm to RT
  3. stirringis stirred until liquid chromatography/mass spectrometry (LC/MS)
  4. customconversion of the starting material (1 hour)
  5. customA yellow suspension is formed
  6. stirringThe mixture is stirred for 30 h
  7. filtrationfiltered
  8. washthe solid is rinsed with water
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-8278b466fee547168094d2ec1efbfba5
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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