Sodium Iodide → 4-tert-Butyl-5-chloro-3,4-dihydro-1H-quinoxalin-2-one

HRID 558963노트

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HRID 558963 반응식
Br[CH2:2][C:3](Br)=[O:4].[C:6]([NH:10][C:11]1[C:12]([NH2:18])=[CH:13][CH:14]=[CH:15][C:16]=1[Cl:17])([CH3:9])([CH3:8])[CH3:7].C(N(C(C)C)CC)(C)C.[I-].[Na+]>C1COCC1.C(#N)C>[C:6]([N:10]1[C:11]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[Cl:17])[NH:18][C:3](=[O:4])[CH2:2]1)([CH3:9])([CH3:7])[CH3:8]

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 61147Bromoacetyl bromideHCID 81531Diisopropylethylamine2회HCID 10845671N*2*-tert-Butyl-3-chlorobenzene-1,2-diamine

생성물 1

HCID 107763594-tert-Butyl-5-chloro-3,4-dihydro-1H-quinoxalin-2-one

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

Bromoacetyl bromide (2.8 ml, 32 mmol) was added drop wise to a solution of N*2*-tert-butyl-3-chlorobenzene-1,2-diamine from Example 12B (4.1 g, 21 mmol) and diisopropylethylamine (11 ml, 63 mmol) in THF (75 ml) while cooling to −78° C. The mixture was allowed to warm to room temperature over 18 h and the solvent was evaporated. Chloroform was added and the mixture was washed with sodium hydrogen carbonate, dried and evaporated. To the residue were added acetonitrile (90 ml), diisopropylethylamine (5.6 ml, 32 mmol) and sodium iodide (3.2 g, 21 mmol). The mixture was heated at reflux for 18 h, cooled and evaporated. The residue was taken up in chloroform, washed with water, dried and evaporated. The residue was purified by flash chromatography on silica (eluant pet.ether:EtOAc 100:0 to 50:50) to give an orange solid; yield 1.5 g, 29%.

후처리

  1. temperatureto warm to room temperature over 18 h
  2. customthe solvent was evaporated
  3. additionChloroform was added
  4. washthe mixture was washed with sodium hydrogen carbonate
  5. customdried
  6. customevaporated
  7. temperatureThe mixture was heated
  8. temperatureat reflux for 18 h
  9. temperaturecooled
  10. customevaporated
  11. washwashed with water
  12. customdried
  13. customevaporated
  14. customThe residue was purified by flash chromatography on silica (eluant pet.ether:EtOAc 100:0 to 50:50)
  15. customto give an orange solid

출처 및 근거

ORD 기록
ord-e8d2fa7a7b8e41168729d93262cfea04
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063038B2

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