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

HRID 1991260ノート

反応式

HRID 1991260 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-70a6fd12212b4a8f86936b7a655ab0bd
出典データセット
uspto-grants-2010_01
特許番号
US07645781B2

反応ノート

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