4-t-Butylbenzenesulfonyl chloride → 4-tert-butyl-N-(4-chloro-2-isonicotinoylphenyl)benzenesulfonamide

HRID 2409112

反応式

HRID 2409112 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:10].[C:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])([CH3:19])[CH3:18]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([S:27]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=2[C:9](=[O:10])[C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)(=[O:29])=[O:28])=[CH:23][CH:22]=1)([CH3:20])([CH3:18])[CH3:19]

参加物

5

反応物 2

HCID 1398824-t-Butylbenzenesulfonyl chloride2 回HCID 10214538(2-Amino-5-chlorophenyl)-pyridin-4-yl methanone

生成物 1

HCID 98239374-tert-butyl-N-(4-chloro-2-isonicotinoylphenyl)benzenesulfonamide収率 56.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

反応条件

温度
60 °C

実験手順

A suspension of (2-amino-5-chlorophenyl) (pyridin-4-yl)methanone (156 g) in pyridine (2350 mL) was heated at 60° C. N,N-Dimethyl-4-aminopyridine (8.21 g) and 4-tert-butylbenzenesulfonyl chloride (180 g) were added, and the mixture was heated at 75° C. for 18 hr. 4-tert-Butylbenzenesulfonyl chloride (15.6 g) was further added, and the mixture was stirred for 1 hr, and this operation was repeated 6 times. The solvent was evaporated under reduced pressure, ethyl acetate was added, and the mixture was washed twice with water (500 mL), and twice with saturated aqueous sodium hydrogen carbonate solution (500 mL). The organic layer was washed twice with 2N hydrochloric acid (200 mL), once with saturated aqueous sodium hydrogen carbonate solution (500 mL), and once with saturated brine (500 mL). The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, 2-propanol was added to the residue and the mixture was stirred at 50° C. for 1 hr. After cooling, the solid was washed with cold 2-propanol (600 mL) and hexane, and dried. 2-Propanol/ethyl acetate (800 mL/80 mL) was added, and the mixture was stirred at 50° C. for 1 hr. After cooling, the solid was washed with cold 2-propanol and hexane, and dried to give the object 4-tert-butyl-N-(4-chloro-2-isonicotinoylphenyl)benzenesulfonamide (162 g, pale-yellow solid). The filtrate was purified by silica gel column chromatography (ethyl acetate/chloroform) to give the object 4-tert-butyl-N-(4-chloro-2-isonicotinoylphenyl)benzenesulfonamide (29 g, pale-yellow solid). A total of 191 g of the object product 4-tert-butyl-N-(4-chloro-2-isonicotinoylphenyl)benzenesulfonamide was obtained.

後処理

  1. temperaturethe mixture was heated at 75° C. for 18 hr
  2. customThe solvent was evaporated under reduced pressure, ethyl acetate
  3. additionwas added
  4. washthe mixture was washed twice with water (500 mL)
  5. washThe organic layer was washed twice with 2N hydrochloric acid (200 mL), once with saturated aqueous sodium hydrogen carbonate solution (500 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure, 2-propanol
  8. additionwas added to the residue
  9. stirringthe mixture was stirred at 50° C. for 1 hr
  10. temperatureAfter cooling
  11. washthe solid was washed with cold 2-propanol (600 mL) and hexane
  12. customdried
  13. addition2-Propanol/ethyl acetate (800 mL/80 mL) was added
  14. stirringthe mixture was stirred at 50° C. for 1 hr
  15. temperatureAfter cooling
  16. washthe solid was washed with cold 2-propanol and hexane
  17. customdried

出典と根拠

ORDレコード
ord-1bd3309436954ae588a09f33e6279f6f
出典データセット
uspto-grants-2014_08
特許番号
US08815887B2

関連ノート

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