N-Acetylsulfanilyl chloride → N-(4-(N-1,3,4-thiadiazol-2-ylsulfamoyl)phenyl)acetamide

HRID 1966878ノート

反応式

HRID 1966878 の反応式
[NH2:1][C:2]1[S:3][CH:4]=[N:5][N:6]=1.[C:7]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1)(=[O:9])[CH3:8]>N1C=CC=CC=1.Cl>[S:3]1[CH:4]=[N:5][N:6]=[C:2]1[NH:1][S:17]([C:14]1[CH:13]=[CH:12][C:11]([NH:10][C:7](=[O:9])[CH3:8])=[CH:16][CH:15]=1)(=[O:19])=[O:18]

参加物

5

反応物 2

HCID 8481N-Acetylsulfanilyl chlorideHCID 199091,3,4-Thiadiazol-2-amine

生成物 1

HCID 694845N-(4-(N-1,3,4-thiadiazol-2-ylsulfamoyl)phenyl)acetamide収率 95%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 1049Pyridine溶媒

反応条件

温度
95 °C

実験手順

2-Amino-1,3,4-thiadiazole (500 mg, 4.95 mmol) was suspended in pyridine (1.26 mL). p-Acetamidobenzenesulfonyl chloride (1.2 g, 5.15 mmol) was added and the mixture was heated to 95° C. for 1 h. The mixture was dissolved in 10% aqueous HCl and extracted with ethyl acetate. The organic extracts were washed with water and dried over anhydrous Na2SO4. Evaporation of the solvent yielded the crude product (1.4 g, 4.7 mmol, 95%). Recrystallization from CH2Cl2/MeOH gave pure product, mp 216-217° C. (lit1 mp 214-215° C.); 1H NMR (250 MHz, CDCl3) δ 2.07 (3, s), 7.73 (4, s), 8.74 (1, s), 10.35 (1, s), 14.35 (1, br s); 13C NMR (62.5 MHz, DMSO) δ 24.2, 118.7, 127.0, 135.6, 143.0, 144.9, 167.2, 169.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe organic extracts were washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-61ac95935232490e914d657273988bb1
出典データセット
uspto-grants-2013_04
特許番号
US08420678B2

反応ノート

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