Chloroacetyl chloride → 6-Bromo-2H-1,4-benzoxazin-3(4H)-one

HRID 417916

반응식

HRID 417916 반응식
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[C:13]([Br:15])[CH:12]=[CH:11][C:10]=1[OH:16].Cl[CH2:18][C:19](Cl)=[O:20].[H-].[Na+]>C1COCC1>[Br:15][C:13]1[CH:12]=[CH:11][C:10]2[O:16][CH2:18][C:19](=[O:20])[NH:8][C:9]=2[CH:14]=1

참가 물질

6

반응물 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 3518402-Amino-4-Bromophenol

생성물 1

HCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-one수율 72.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Triethylamine (2.4 mL, 17 mmol) was added to 2-amino-4-bromophenol (2.5 g, 13 mmol) in THF (80 mL). The reaction was cooled in ice and chloroacetyl chloride (1.12 mL, 14 mmol) added portionwise. It was stirred with cooling for 10 min then allowed to warm to r.t. and stirred for a further 2 h. The reaction mixture was cooled in ice and sodium hydride (1.05 g of a 60% suspension in oil, 26 mmol) was added portionwise. The mixture was stirred with ice-bath cooling for 20 min then at r.t. for 2 h before being quenched with water (20 mL). The THF was removed in vacuo and the resulting mixture diluted with water (100 mL). The precipitate was filtered off, washed with water (3×50 mL) and dried in vacuo to yield the title compound as a beige solid (2.14 g, 70%). δH (DMSO-d6) 4.60 (2H, s), 6.92 (1H, d, J 8.5 Hz), 7.02 (1H, d, J 2.3 Hz), 7.08 (1H, dd, J 8.5, 2.3 Hz), 10.81 (1H, br s).

후처리

  1. temperatureThe reaction was cooled in ice
  2. temperaturewith cooling for 10 min
  3. stirringstirred for a further 2 h
  4. temperatureThe reaction mixture was cooled in ice
  5. stirringThe mixture was stirred with ice-bath
  6. temperaturecooling for 20 min
  7. customat r.t. for 2 h before being quenched with water (20 mL)
  8. customThe THF was removed in vacuo
  9. additionthe resulting mixture diluted with water (100 mL)
  10. filtrationThe precipitate was filtered off
  11. washwashed with water (3×50 mL)
  12. customdried in vacuo

출처 및 근거

ORD 기록
ord-181b1dc58ad645a9803fe02194e08224
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093238B2

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