Acetone → 4-Tert-butyl-n-(4-chloro-2-(5-methyl-1h-1,2,3-triazol-1-yl)phenyl)benzenesulfonamide

HRID 502837Notes

Reaction equation

HRID 502837 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N:22]2[C:26]([CH3:27])=[C:25](I)[N:24]=[N:23]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CC(C)=O>>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[N:22]2[C:26]([CH3:27])=[CH:25][N:24]=[N:23]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 180AcetoneHCID 59428119HCID 59428119, compound

Product 1

HCID 573779714-Tert-butyl-n-(4-chloro-2-(5-methyl-1h-1,2,3-triazol-1-yl)phenyl)benzenesulfonamide

Procedure

4-tert-butyl-N-(4-chloro-2-(4-iodo-5-methyl 1H-1,2,3-triazol-1-yl)phenyl)benzenesulfonamide (synthesized according to general procedure P, 75 mg, 0.14 mmol) was placed in a 10 mL 2-neck flask and the flask was evacuated and purged with N2 three times. To the solid was added THF (0.71 mL) and the solution was lowered to −78° C. PhMgBr (0.079 mL, 1.8 M) was added to the solution and it was stirred for 15 minutes. n-BuLi (0.069 mL, 2.0 M) was subsequently added and the reaction was stirred an additional 60 minutes. Acetone (0.042 mL, 0.57 mmol) was added to the reaction and it was warmed to ambient temperature. The solution was subsequently partitioned with EtOAc/10% HCl and the aqueous layer was extracted three times with EtOac. The combined organics were dried over sodium sulfate, concentrated in vacuo, and purified by HPLC to afford the desired triazole: MS (ES) M+H expected 405.1, found 405.4.

Workup

  1. customthe flask was evacuated
  2. custompurged with N2 three times
  3. additionTo the solid was added THF (0.71 mL)
  4. customwas lowered to −78° C
  5. additionPhMgBr (0.079 mL, 1.8 M) was added to the solution and it
  6. additionn-BuLi (0.069 mL, 2.0 M) was subsequently added
  7. stirringthe reaction was stirred an additional 60 minutes
  8. customThe solution was subsequently partitioned with EtOAc/10% HCl
  9. extractionthe aqueous layer was extracted three times with EtOac
  10. dry with materialThe combined organics were dried over sodium sulfate
  11. concentrationconcentrated in vacuo
  12. custompurified by HPLC

Sources & evidence

ORD record
ord-91ada6d4631940729c7b69d0527a2222
Source dataset
uspto-grants-2010_08
Patent number
US07776877B2

Reaction notes

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