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

HRID 513605노트

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HRID 513605 반응식
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

참가 물질

4

반응물 2

HCID 10906Tert-Butyl nitriteHCID 681834662-Amino-N-(4-chloro-quinolin-8-yl)-benzenesulfonamide2회

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6ba6e3f86ae041d9b71cca0cde9eab77
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102688B2

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