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4-Nitrobenzenesulfonyl chloride → (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-nitrobenzenesulfonamide

HRID 2302084
ノート
印刷プレビュー

反応式

HRID 2302084 の反応式
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][CH:8]([NH2:11])[CH2:9][CH3:10].C(N(CC)CC)C.[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1)([O-:21])=[O:20]>C(Cl)Cl>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH2:7][C@H:8]([NH:11][S:28]([C:25]1[CH:24]=[CH:23][C:22]([N+:19]([O-:21])=[O:20])=[CH:27][CH:26]=1)(=[O:29])=[O:30])[CH2:9][CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 149997103-Chloro-2-(2-aminobutyl)thiophene

生成物 1

HCID 12070688(R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-nitrobenzenesulfonamide収率 95.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Six grams of 3-chloro-2-(2-aminobutyl)thiophene is dissolved in 10 ml of methylene chloride in a 3-neck round bottomed flask blanketed with an inert atmosphere at 0° C. Triethylamine (6.6 ml) is added in one portion followed by 7.8 g of 4-nitrobenzenesulfonyl chloride which had been previously dissolved in 10 ml of methylene chloride. After stirring for 1 hour at ambient temperature, the methylene chloride is removed under vacuum and 40 ml of methanol is added with warming to dissolve all solids. The resulting solution is poured into cold water, agitated for 30 minutes, filtered and washed with cold water, and the isolated material is dried in a vacuum oven to provide (R)-N-[1-[(3-chlorothien-2-yl)methyl]propyl]-4-nitrobenzenesulfonamide (11.3 g) as a tan solid. MS: m/z (E1, 70EV) 375(10%). 1H NMR (200 MHz; CDCl3): δ 0.95 (3H, t, CH3), 1.7 (2H, m, CH2), 2.85 (2H, m, CH2), 3.5 (1H, m, CH), 6.65 (1H, d, CH), 7.0 (1H, d, CH), 7.9 (2H, d, Ph), 8.2 (2H, d, Ph).

後処理

  1. customblanketed with an inert atmosphere at 0° C
  2. customthe methylene chloride is removed under vacuum and 40 ml of methanol
  3. additionis added
  4. temperaturewith warming
  5. dissolutionto dissolve all solids
  6. additionThe resulting solution is poured into cold water
  7. stirringagitated for 30 minutes
  8. filtrationfiltered
  9. washwashed with cold water
  10. customthe isolated material is dried in a vacuum oven

出典と根拠

ORDレコード
ord-83c682dc9ee741ca9976491500542203
出典データセット
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06429315B1

反応ノート

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