Isopropyl iodide → 6-nitro-3-isopropyl-2(3H)-benzothiazolone

HRID 896124

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HRID 896124 반응식
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].N12CCCN=C1CC[CH2:17][CH2:16][CH2:15]2.IC(C)C>CN(C)C=O.O>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[N:8]([CH:16]([CH3:17])[CH3:15])[C:9](=[O:11])[S:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

참가 물질

6

반응물 3

HCID 6362Isopropyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6415712(3H)-Benzothiazolone, 6-nitro-

생성물 1

HCID 218780606-nitro-3-isopropyl-2(3H)-benzothiazolone

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

A stirred solution of 6-nitro-2-benzothiazolinone (5.0 g, 25.5 mmol) in anhydrous N,N-dimethylformamide (51 mL) under N2 is treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (4.96 mL, 33.1 mmol) dropwise. Following a slight exotherm, the reaction mixture is heated up to 50° C. and treated with 2-iodopropane (12.7 mL, 127 mmol). The resulting mixture is quickly heated up to 75° C., stirred at this temperature for 40 mins, cooled to ambient temperature and diluted with ice (100 mL) and water (100 mL). The precipitate is isolated by filtration and recrystallized from ethyl acetate/hexanes to give the title compound, mp 138-142° C.

후처리

  1. temperatureThe resulting mixture is quickly heated up to 75° C.
  2. temperaturecooled to ambient temperature
  3. customThe precipitate is isolated by filtration
  4. customrecrystallized from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-60dfaa3b7716471bb5b52ba7501987ed
출처 데이터셋
uspto-grants-2005_07
특허 번호
US06919329B2

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