Benzenesulfonyl chloride → HCID 54114989, compound

HRID 368387Notes

Reaction equation

HRID 368387 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH2:10])[C:5]#[N:6].[C:11]1([S:17](Cl)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([N:23](CC)CC)C>C(Cl)Cl>[C:11]1([S:17]([NH:23][NH:10][C:9]2[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][CH:2]=2)(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 7372853,4-Diaminobenzonitrile

Product 1

HCID 54114989HCID 54114989, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,4 diamino benzonitrile (10.7 g, 0.08 mol) in methylene chloride was treated with phenyl sulfonyl chloride (2 eq, 0.16 mol) and triethyl amine (2 eq, 0.16 mol) for 18 hours at 23° C. The reaction mixture was partitioned between water and methylene chloride. The organic layer was separated and dried over sodium sulfate. The solution was filtered and concentrated to 50 mL and a solid was precipitated out with hexanes. This solid was dissolved in tetrahydrofuran and treated with 25% NaOMe in methanol. The reaction was complete after 5 minutes. The reaction mixture was acidified to pH 7 with ammonium chloride solution, then it was extracted with methylene chloride. The organic layer was dried over magnesium sulfate, filtered and concentrated to 50 mL. Hexanes were added to precipitate desired as a white solid (19.7 grams).

Workup

  1. customThe reaction mixture was partitioned between water and methylene chloride
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. concentrationconcentrated to 50 mL
  6. customa solid was precipitated out with hexanes
  7. dissolutionThis solid was dissolved in tetrahydrofuran
  8. additiontreated with 25% NaOMe in methanol
  9. extractionit was extracted with methylene chloride
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated to 50 mL
  13. additionHexanes were added
  14. customto precipitate

Sources & evidence

ORD record
ord-dc03da8d334c4546bbcbbb4bce1fc884
Source dataset
uspto-grants-2000_10
Patent number
US06133319

Reaction notes

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