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Cyclopentanol → 12-Chloro-9-cyclopentyloxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513769
ノート
印刷プレビュー

反応式

HRID 513769 の反応式
[H-].[Na+].[CH:3]1([OH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:9][C:10]1[CH:11]=[C:12]2[C:21](=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[N:23]3)[NH:20][S:19](=[O:29])(=[O:28])[C:18]1[C:13]2=[CH:14][C:15](F)=[CH:16][CH:17]=1.OS([O-])(=O)=O.[K+]>CN1C(=O)CCC1>[Cl:9][C:10]1[CH:11]=[C:12]2[C:21](=[C:22]3[C:27]=1[CH:26]=[CH:25][CH:24]=[N:23]3)[NH:20][S:19](=[O:29])(=[O:28])[C:18]1[C:13]2=[CH:14][C:15]([O:8][CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)=[CH:16][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7298CyclopentanolHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 6818318212-Chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

生成物 1

HCID 6016476112-Chloro-9-cyclopentyloxy-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide収率 20%

試薬・触媒・溶媒 1

HCID 13387
N-methyl-2-pyrrolidone
溶媒

実験手順

NaH (60% in mineral oil; 53 mg, 1.34 mmol) was added to a solution of cyclopentanol (115 mg, 1.34 mmol) in NMP (3 ml) and the mixture was stirred at room temperature for 15 min. 12-chloro-9-fluoro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide 503 (150 mg, 0.44 mmol) was added and the mixture was heated at 180 C in a microwave for 2 h. After cooling, the mixture was poured into ice cold water and neutralized using sat aq. KHSO4 solution. The resulting precipitate was collected by filtration and dried. The crude solid was purified by column chromatography with n-hexane/DCM (30:70) as the eluent to give the title compound (23 mg, 20%).

後処理

  1. temperaturethe mixture was heated at 180 C in a microwave for 2 h
  2. temperatureAfter cooling
  3. additionthe mixture was poured into ice cold water
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried
  6. customThe crude solid was purified by column chromatography with n-hexane/DCM (30:70) as the eluent

出典と根拠

ORDレコード
ord-c4d73bf1d803409f93ac5ccb34dbfd6c
出典データセット
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09102688B2

反応ノート

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