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

HRID 393829

반응식

HRID 393829 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f622c312826c4955b8b81db1e9b3f7e5
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06809119B2

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