2-Mesitylenesulfonyl chloride → 1-(2,4,6-Trimethylbenzenesulphonyl)-1H-indazole-3-carboxylic acid

HRID 1454927

반응식

HRID 1454927 반응식
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[N:4]1.[C:15]1([CH3:27])[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[S:23](Cl)(=[O:25])=[O:24]>CN(C=O)C.O1CCCC1>[CH3:27][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:16]=1[S:23]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[N:4]1)(=[O:24])=[O:25]

참가 물질

6

반응물 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 24758Sodium hydrideHCID 78250Indazole-3-carboxylic acid

생성물 1

HCID 121060701-(2,4,6-Trimethylbenzenesulphonyl)-1H-indazole-3-carboxylic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

NaH (60% in oil, 40 mmol) is washed under argon with petroleum ether and then suspended in 60 ml of anhydrous DMF. An indazole-3-carboxylic acid solution (3.35 g, 20 mmol) in anhydrous DMF (50 ml) is added dropwise to this suspension kept at 0° C. The reaction mixture becomes clear. When the addition is complete, the medium is allowed to react for 30 min at room temperature and then the reaction mixture is again cooled to 0° C. Mesitylenesulphonyl chloride (4.82 g, 22 mmol) in solution in anhydrous tetrahydrofuran (THF) (50 ml) is added. The ice bath is removed and a suspension appears. The medium is allowed to react for 30 min at room temperature. The solvents are evaporated under vacuum and the residue is taken up in 0.1N NaOH solution. The solution obtained is washed with diethyl ether and then acidified with 6N HCl. The compound which separates is filtered, and taken up in AcOEt. The AcOEt solution is dried over Na2SO4 and then evaporated. The residue (6.18 g) is recrystallized from AcOEt/petroleum ether.

후처리

  1. customkept at 0° C
  2. additionWhen the addition
  3. customto react for 30 min at room temperature
  4. customThe ice bath is removed
  5. customto react for 30 min at room temperature
  6. customThe solvents are evaporated under vacuum
  7. customThe solution obtained
  8. washis washed with diethyl ether
  9. filtrationThe compound which separates is filtered
  10. dry with materialThe AcOEt solution is dried over Na2SO4
  11. customevaporated
  12. customThe residue (6.18 g) is recrystallized from AcOEt/petroleum ether

출처 및 근거

ORD 기록
ord-71a6a69b58b34eba9167559fac26177c
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07482342B2

연결된 노트

불러오는 중…