Sulfuric Acid → HCID 13824262, compound

HRID 1906853Notes

Reaction equation

HRID 1906853 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][N:12]2[C:17]([C:18]3[CH:19]=[C:20]([N:24]([CH3:35])S(C4C=CC(C)=CC=4)(=O)=O)[CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:15]=[N:14][C:13]=12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.S(=O)(=O)(O)O.[OH-].[Na+]>>[CH3:35][NH:24][C:20]1[CH:19]=[C:18]([C:17]2[N:12]3[N:11]=[CH:10][C:9]([C:1]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[O:8])=[C:13]3[N:14]=[CH:15][CH:16]=2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 13824261HCID 13824261, compound

Product 1

HCID 13824262HCID 13824262, compound

Procedure

Five grams of N-[3-(3-benzoylpyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N,4-dimethylbenzenesulfonamide was added to a mixture of 50 ml of trifluoroacetic acid and 10 ml of concentrated sulfuric acid. This mixture was heated at the boiling point under reflux for 3 hours. It was then poured onto 300 g of ice containing 150 ml of 10N sodium hydroxide solution. The yellow precipitate that formed was collected, washed with water, and air dried. It was dissolved in 100 ml of methylene chloride, the solution dried over magnesium sulfate, and the methylene chloride was then removed in vacuo. A bright yellow residue of 3.4 g of the desired compound was left, mp 134°-136° C.

Workup

  1. temperatureThis mixture was heated at the boiling point
  2. temperatureunder reflux for 3 hours
  3. customThe yellow precipitate that formed
  4. customwas collected
  5. washwashed with water, and air
  6. customdried
  7. dissolutionIt was dissolved in 100 ml of methylene chloride
  8. dry with materialthe solution dried over magnesium sulfate
  9. customthe methylene chloride was then removed in vacuo
  10. waitA bright yellow residue of 3.4 g of the desired compound was left

Sources & evidence

ORD record
ord-f61bb28a4a234312bd28c3b8442120f8
Source dataset
uspto-grants-1987_03
Patent number
US04654347

Reaction notes

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