Trichloroacetyl isocyanate → 7-Benzyloxy-2-ethylthiazolo[4,5-c]quinolin-4-amine

HRID 913358노트

반응식

HRID 913358 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:22][C:21]([CH2:23][CH3:24])=[N:20][C:14]=3[CH:15]=[N+:16]([O-])[C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC(Cl)(Cl)C([N:29]=C=O)=O>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:22][C:21]([CH2:23][CH3:24])=[N:20][C:14]=3[C:15]([NH2:29])=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 76400Trichloroacetyl isocyanateHCID 673930907-Benzyloxy-2-ethylthiazolo[4,5-c]quinoline 5-oxide

생성물 1

HCID 589650297-Benzyloxy-2-ethylthiazolo[4,5-c]quinolin-4-amine수율 75.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a vigorously stirred pale orange solution of 7-benzyloxy-2-ethylthiazolo[4,5-c]quinoline 5-oxide (15.00 g, 44.6 mmol) in dichloromethane (200 mL), at room temperature, was slowly added trichloroacetylisocyanate (1.05 eq., 5.6 ml 46.8 mmol). The solution was maintained at room temperature for 18 hours. At this time the reaction was quenched by the addition of concentrated ammonium hydroxide solution (60 ml). An off-white precipitate formed and was collected by vacuum filtration. Recrystallization from acetonitrile provided 11.3 g of 7-benzyloxy-2-ethylthiazolo[4,5-c]quinolin-4-amine as a white crystalline solid, mp 208-209° C. MS (APCI) m/z 336.1 (M+H)+; Anal. calcd for C19H17N3OS: C, 68.03; H, 5.11; N, 12.53. Found: C, 67.45; H, 4.83; N, 12.41.

후처리

  1. customat room temperature
  2. customAt this time the reaction was quenched by the addition of concentrated ammonium hydroxide solution (60 ml)
  3. customAn off-white precipitate formed
  4. filtrationwas collected by vacuum filtration
  5. customRecrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-4bdc6ca2cce84d188e98acf77f584c91
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026366B2

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