Acetaldehyde → 4-tert-butyl-N-(4-chloro-2-(4-(1-hydroxyethyl)-5-methyl-1H-1,2,3-triazol-1-yl)phenyl)benzenesulfonamide

HRID 76016Notes

Reaction equation

HRID 76016 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].[CH:29](=[O:31])[CH3:30]>>[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]([CH:29]([OH:31])[CH3:30])[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 177AcetaldehydeHCID 59428119HCID 59428119, compound

Product 1

HCID 573779724-tert-butyl-N-(4-chloro-2-(4-(1-hydroxyethyl)-5-methyl-1H-1,2,3-triazol-1-yl)phenyl)benzenesulfonamide

Conditions

Temperature
0 °C

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, 200 mg, 0.38 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 (1.9 mL) and the solution was lowered to −78° C. PhMgBr (0.21 mL, 1.8 M) was added to the solution and it was stirred for 15 minutes. n-BuLi (0.19 mL, 2.0 M) was subsequently added and the reaction was stirred an additional 30 minutes. Acetaldehyde (0.085 mL, 1.5 mmol) was added to the reaction and it was warmed to 0° C. The solution was subsequently quenched with 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 4-tert-butyl-N-(4-chloro-2-(4-(1-hydroxyethyl)-5-methyl-1H-1,2,3-triazol-1-yl)phenyl)benzenesulfonamide as a white solid: MS (ES) M+H expected 449.1, found 449.1.

Workup

  1. customthe flask was evacuated
  2. custompurged with N2 three times
  3. additionTo the solid was added THF (1.9 mL)
  4. customwas lowered to −78° C
  5. additionPhMgBr (0.21 mL, 1.8 M) was added to the solution and it
  6. additionn-BuLi (0.19 mL, 2.0 M) was subsequently added
  7. stirringthe reaction was stirred an additional 30 minutes
  8. customThe solution was subsequently quenched with 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-5c7c8c20f0ce46e89d917ae5a32d7938
Source dataset
uspto-grants-2014_09
Patent number
US08835468B2

Reaction notes

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