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

HRID 1480921ノート

反応式

HRID 1480921 の反応式
[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]

参加物

3

反応物 2

HCID 177AcetaldehydeHCID 59428119HCID 59428119、化合物

生成物 1

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

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5641240b7c0f4e5aac0555ca3ba64705
出典データセット
uspto-grants-2016_08
特許番号
US09409909B2

反応ノート

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