Diisopropylethylamine → HCID 58727302, 화합물

HRID 502556노트

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HRID 502556 반응식
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([NH:12][CH2:13][CH2:14][NH2:15])[C:8]=2[CH:16]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.Cl.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33](Cl)=[O:34]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][N:10]=[C:9]([NH:12][CH2:13][CH2:14][NH:15][C:33](=[O:34])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][N:27]=3)[C:8]=2[CH:16]=1)([O-:3])=[O:2]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 58727034N1-(5-nitrobenzo[d]isothiazol-3-yl)ethane-1,2-diamine

생성물 1

HCID 58727302HCID 58727302, 화합물수율 76.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

N1-(5-Nitrobenzo[d]isothiazol-3-yl)ethane-1,2-diamine (92 mg, 0.38 mmol) was dissolved in anhydrous dichloromethane (5 mL) with diisopropylethylamine (148 μL, 1.3 mmol). The solution was cooled on an ice-water bath and a solution of 2-picolinoyl chloride hydrochloride (76 mg, 2.7 mmol) in dichloromethane (0.5 mL) was added dropwise. The reaction mixture was allowed to stir for 2.5 h while warming to room temperature. The solution was diluted with dichloromethane, washed with saturated sodium bicarbonate solution, then dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure to yield N-(2-(5-nitrobenzo[d]isothiazol-3-ylamino)ethyl)picolinamide (100 mg) as a yellow solid. 1H NMR (300 MHz, CDCl3): 8.58 (m, 1H), 8.40 (m, 1H), 8.22 (d, 1H), 7.83 (t, 1H), 7.45 (m, 2H), 7.40 (m, 2H), 3.80 (m, 2H), 3.60 ppm (m, 2H). MW=343 confirmed by LC-MS, tr=11.59 min (Method Y) MH+=344.

후처리

  1. temperatureThe solution was cooled on an ice-water bath
  2. washwashed with saturated sodium bicarbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6bec3d83150b4b688d0684ec46ec3b26
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776847B2

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