Tert-Butyl nitrite → 1-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide

HRID 513605ノート

反応式

HRID 513605 の反応式
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:13]=[CH:14][CH:15]=[C:16]2[C:21]=1[N:20]=[CH:19][CH:18]=[C:17]2[Cl:22])(=[O:10])=[O:9].N(OC(C)(C)C)=O>CC(O)=O>[Cl:22][C:17]1[C:16]2[C:21](=[C:12]3[C:13](=[CH:14][CH:15]=2)[C:4]2[C:3](=[CH:2][CH:7]=[CH:6][CH:5]=2)[S:8](=[O:10])(=[O:9])[NH:11]3)[N:20]=[CH:19][CH:18]=1

参加物

4

反応物 2

HCID 10906Tert-Butyl nitriteHCID 681834662-Amino-N-(4-chloro-quinolin-8-yl)-benzenesulfonamide2 回

生成物 1

HCID 681833551-Chloro-5H-6-thia-4,5-diaza-chrysene 6,6-dioxide収率 33%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
0 °C

実験手順

2-Amino-N-(4-chloro-quinolin-8-yl)-benzenesulfonamide (Intermediate 275) (1.3 g, 3.89 mmol) was dissolved in AcOH (13 ml) and the mixture was stirred at 0° C. for 5 min. The solution was cooled to −10° C. and t-butyl nitrite (0.7 ml, 5.83 mmol) was added dropwise and the mixture was stirred at room temperature 30 min. The mixture was quenched with sat. NaHCO3 solution and the aqueous phase was extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (400 mg, 33%) after the purification by column chromatography with DCM/MeOH (90:10) as the eluent.

後処理

  1. temperatureThe solution was cooled to −10° C.
  2. stirringthe mixture was stirred at room temperature 30 min
  3. customThe mixture was quenched with sat. NaHCO3 solution
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-6ba6e3f86ae041d9b71cca0cde9eab77
出典データセット
uspto-grants-2015_08
特許番号
US09102688B2

反応ノート

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