Sulfuric Acid → HCID 178500118, compound

HRID 2065784Notes

Reaction equation

HRID 2065784 reaction equation
N[C:2]1[N:7]=[C:6]([C:8]2[N:9]=[C:10]([C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=2[F:20])[CH:5]=[CH:4][C:3]=1[N+:28]([O-:30])=[O:29].S(=O)(=O)(O)[OH:32].N([O-])=O.[Na+]>CS(C)=O.O>[F:20][C:14]1[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]=1[C:12]1[NH:11][C:10]([C:21]([CH3:26])([CH3:27])[C:22]([O:24][CH3:25])=[O:23])=[N:9][C:8]=1[C:6]1[CH:5]=[CH:4][C:3]([N+:28]([O-:30])=[O:29])=[C:2]([OH:32])[N:7]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 23668193Sodium NitriteHCID 178500116HCID 178500116, compound

Product 1

HCID 178500118HCID 178500118, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 2-[4-(6-amino-5-nitro-2-pyridyl)-5-(2,4-difluorophenyl)-1H-imidazol-2-yl]-2-methyl-propanoate (56 g, 134.17 mmol) in dimethyl sulfoxide (DMSO, 400 mL) and water (320 mL), is added sulfuric acid 95-97% (80 mL) dropwise. Then the mixture is cooled to 0° C. To the above mixture a solution of sodium nitrite (18.70 g, 268.35 mmol) in water (80 mL) is added dropwise over 15 min at 0° C. The reaction mixture is stirred for 20 min at that temperature and then the cooling bath is removed and the temperature is allowed to rise to RT. To the reaction mixture is added a 0.8 M aqueous solution of buffered sodium phosphate monobasic (1200 mL, pH=6). A yellow suspension appears. This suspension is stirred at RT for 1 h. The solid is filtered, washed with water, and dried in the oven to afford the title compound as an orange solid (49.5 g, 88%). LC-ES/MS m/z 419 (M+1).

Workup

  1. customthe cooling bath is removed
  2. customto rise to RT
  3. additionTo the reaction mixture is added a 0.8 M aqueous solution of buffered sodium phosphate monobasic (1200 mL, pH=6)
  4. stirringThis suspension is stirred at RT for 1 h
  5. filtrationThe solid is filtered
  6. washwashed with water
  7. customdried in the oven

Sources & evidence

ORD record
ord-f1ddca763a4149cfbb4553963d638397
Source dataset
uspto-grants-2012_10
Patent number
US08288548B2

Reaction notes

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