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

HRID 913358ノート

反応式

HRID 913358 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4bdc6ca2cce84d188e98acf77f584c91
出典データセット
uspto-grants-2011_09
特許番号
US08026366B2

反応ノート

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