4-Chlorobenzenesulfonyl chloride → 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide

HRID 1011551노트

반응식

HRID 1011551 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2([CH2:19][OH:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 409153(1-Aminocyclohexyl)methanol

생성물 1

HCID 210787144-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide수율 73.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Chlorobenzenesulfonyl chloride (6.92 g, 32.8 mmol) was added to a solution of (1-aminocyclohexyl)methanol (prepared according to Helv. Chirp. Acta, 87:90-105 (2004)) (3.53 g, 27.3 mmol) and triethylamine (4.6 mL, 32.8 mmol) in 100 mL tetrahydrofuran at room temperature. The reaction was stirred overnight and concentrated. The residue was taken up in a mixture of 100 mL ethyl acetate and 100 mL brine. The organic layer was separated, dried over sodium sulfate, and purified by flash chromatography on 120 g silica gel with 20 to 100% ethyl acetate in hexane to yield 4-chloro-N-(1-(hydroxymethyl)cyclohexyl)benzenesulfonamide (6.07 g, 73%). 1H NMR (400 MHz, CDCl3) δ ppm 7.85-7.86 (1H, m), 7.81-7.84 (1H, m), 7.47-7.49 (1H, m), 7.44-7.46 (1H, m), 4.61 (1H, s), 3.60 (2H, d, J=5.54 Hz), 2.25 (1H, t, J=5.92 Hz), 1.57-1.69 (2H, m), 1.22-1.45 (8H, m). LC/MS R.T.=2.39 min; [M+H]+=304.03; [M+Na]+=326.05; [M−H]−=301.98.

후처리

  1. concentrationconcentrated
  2. additionThe residue was taken up in a mixture of 100 mL ethyl acetate and 100 mL brine
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. custompurified by flash chromatography on 120 g silica gel with 20 to 100% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-2397997a49be4845b8e6fd22bf96a569
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977362B2

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