Nitronium → HCID 178504683, 화합물

HRID 423606노트

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HRID 423606 반응식
N([O-])=O.[Na+].[CH3:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[CH:17][C:18](N)=[N:19][CH:20]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7].[O:22]=[N+]=O>OS(O)(=O)=O>[CH3:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]=[CH:17][C:18]([OH:22])=[N:19][CH:20]=2)=[CH:11][CH:10]=1)(=[O:8])=[O:7]

참가 물질

5

반응물 3

HCID 3609161NitroniumHCID 23668193Sodium Nitrite2회HCID 580843845-[4-(Methylsulfonyl)phenyl]-2-pyrazinamine

생성물 1

HCID 178504683HCID 178504683, 화합물수율 81%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매2회

반응 조건

온도
0 °C

실험 절차

NaNO2 (0.20 g, 2.76 mmol) was added in portions to concentrated H2SO4 (1.4 mL) at 0° C. The mixture was heated at 50° C. until all of the NaNO2 had dissolved and the mixture was again cooled to 0° C. A solution of 5-[4-(methylsulfonyl)phenyl]-2-pyrazinamine (0.51 g, 2.05 mmol) in concentrated H2SO4 (4.2 mL) was added dropwise to the nitronium solution. The ice bath was removed, and the mixture was warmed to ambient temperature and stirred for 15 min, then heated to 45° C. for 30 min. The mixture was cooled to ambient temperature and poured into ice water. The pH was adjusted to about 4 with 4N NaOH and the solid was collected, washed with water, and air dried to give 0.415 g (81%) of 5-[4-(methylsulfonyl)phenyl]-2-pyrazinol (and tautomers thereof) as a brown solid. 1H NMR (400 MHz, DMSO-d6): δ 12.77 (bs, 1H), 8.30-8.05 (m, 4H), 7.92 (d, 2H, J=8.6 Hz), 3.21 (s, 3H); LRMS (ESI), m/z 251 (M+H).

후처리

  1. dissolutionhad dissolved
  2. customThe ice bath was removed
  3. temperaturethe mixture was warmed to ambient temperature
  4. temperatureheated to 45° C. for 30 min
  5. temperatureThe mixture was cooled to ambient temperature
  6. additionpoured into ice water
  7. customthe solid was collected
  8. washwashed with water, and air
  9. customdried

출처 및 근거

ORD 기록
ord-d67b34d8e8ba4077938469a358cfe7f8
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08101634B2

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