Benzenesulfonyl chloride → 4-(1,1-Dimethylethyl)-benzoic acid, 2-(phenylsulfonyl)hydrazide

HRID 393829

反応式

HRID 393829 の反応式
[C:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([NH:11][NH2:12])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[C:24]1([S:30](Cl)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.CN(C1C=CN=CC=1)C>[C:24]1([S:30]([NH:12][NH:11][C:9](=[O:10])[C:8]2[CH:13]=[CH:14][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)(=[O:32])=[O:31])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 3

HCID 7369Benzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 123513Benzoic acid, 4-(1,1-dimethylethyl)-, hydrazide

生成物 1

HCID 9235034-(1,1-Dimethylethyl)-benzoic acid, 2-(phenylsulfonyl)hydrazide

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

4-tert-Butyl-benzoic acid hydrazide (0.5 g, 2.60 mmol) was dissolved in THF (29 mL). N,N-diisopropylethylamine (1.81 mL, 10.4 mmol) was added, and the reaction was cooled to 0° C. Phenylsulfonyl chloride (0.36 mL, 2.86 mmol) was added followed by DMAP (5 mg, 0.04 mmol). The reaction was allowed to warm to room temperature, and the reactants all dissolved. The solution went from a yellow color to a deep red over the course of 4 hours. The reaction was then concentrated down and purified by flash chromatography eluting with 3:1 hexanes/EtOAc. The desired product was isolated (0.32 g, 37.1%). MS: 333.1 (M+1 for C17H20N2O3S); mp 197-199° C.; TLC: SiO2 Rf=0.56 (1:1 hexane/EtOAc). Analysis C17H20N2O3S: (calc) C, 61.42; H, 6.06; N, 8.43. (found) C, 61.38; H, 6.09; N, 8.27. IR (KBr, cm−1) 3213, 2965, 1648, 1403, 1349, 1179. 1H NMR (400 MHz, CDCl3) δ 1.29 (s, 9H), 7.39-7.55 (m, 8H), 7.92-7.93 (m, 2H), 8.06 (s, 1H).

後処理

  1. temperatureto warm to room temperature
  2. customwent from a yellow color to a deep red over the course of 4 hours
  3. concentrationThe reaction was then concentrated down
  4. custompurified by flash chromatography
  5. washeluting with 3:1 hexanes/EtOAc

出典と根拠

ORDレコード
ord-f622c312826c4955b8b81db1e9b3f7e5
出典データセット
uspto-grants-2004_10
特許番号
US06809119B2

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