Sulfuric Acid → HCID 78103722, compound

HRID 631091Notes

Reaction equation

HRID 631091 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][S:23](=[N:26]C#N)([CH3:25])=[O:24])[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1.S(=O)(=O)(O)O.[OH-].[Na+]>O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][S:23]([CH3:25])(=[NH:26])=[O:24])[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 71535015HCID 71535015, compound

Product 1

HCID 78103722HCID 78103722, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To 780 mg (1.97 mmol) [(3-{[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy}propyl)(methyl)oxido-lambda6-sulfanylidene]cyanamide were added 20 mL 50% aqueous sulfuric acid. It was stirred 2 hours at 140° C. bath temperature. The reaction was allowed to reach room temperature. The sulfuric acid was diluted with 20 mL water and the pH was adjusted to 12 with 50% aqueous sodium hydroxide on an ice bath. The aqueous phase was extracted with 30 mL dichloromethane. During the second extraction water had to be added to separate the layers. The first organic phase was combined with the reaction mixture and vigorously shaken. The layers were separated and the aqueous phase was extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated yielding 530 mg (72%) of a yellow solid.

Workup

  1. customto reach room temperature
  2. extractionThe aqueous phase was extracted with 30 mL dichloromethane
  3. extractionDuring the second extraction water
  4. additionto be added
  5. customto separate the layers
  6. stirringvigorously shaken
  7. customThe layers were separated
  8. extractionthe aqueous phase was extracted three times with dichloromethane
  9. dry with materialThe combined organic layers were dried over sodium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-98c301c6c8914466969b36238ef1e70d
Source dataset
uspto-grants-2016_04
Patent number
US09320737B2

Reaction notes

Loading…