Nitronium → HCID 178504683、化合物

HRID 423606ノート

反応式

HRID 423606 の反応式
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]

参加物

5

反応物 3

HCID 3609161NitroniumHCID 23668193Sodium Nitrite2 回HCID 580843845-[4-(Methylsulfonyl)phenyl]-2-pyrazinamine

生成物 1

HCID 178504683HCID 178504683、化合物収率 81%

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d67b34d8e8ba4077938469a358cfe7f8
出典データセット
uspto-grants-2012_01
特許番号
US08101634B2

反応ノート

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