Nitric Acid → 5-Methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione

HRID 843705

반응식

HRID 843705 반응식
[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[O:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15]>OS(O)(=O)=O>[CH3:1][C:2]1[C:7]2[C:8](=[O:13])[O:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15]

참가 물질

4

반응물 2

HCID 944Nitric AcidHCID 104875225-methyl-2,4-dihydro-1H-3,1-benzoxazine-2,4-dione

생성물 1

HCID 219011545-Methyl-6-nitro-1H-benzo[d][1,3]oxazine-2,4-dione

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

반응 조건

온도
0 °C

실험 절차

To a solution of 5-methyl-4H-3,1-benzoxazin-2,4-dione (20 g, 113 mmol) in 150 mL of concentrated H2SO4, cooled to −15° C., was added 7.83 g of 90% w/w HNO3 (in 30 mL of conc. H2SO4) dropwise at such a rate to keep the internal temperature below 5° C. After the addition was complete, the reaction was stirred at 0° C. for an additional 20 minutes then quenched by pouring the reaction mixture over crushed ice. Following further dilution with water, the resulting precipitate was filtered, washed with water, resuspended in water then filtered and washed again with water affording 15.1 g (60%) of 5-methyl-6-nitro-4H-3,1-benzoxazin-2,4-dione, after drying: Anal. Calc'd. for C9H6N2O5: C, 48.66; H, 2.72; N, 12.61. Found: C, 48.19; H, 2.54; N, 12.51.

후처리

  1. customthe internal temperature below 5° C
  2. additionAfter the addition
  3. customthen quenched
  4. additionby pouring the reaction mixture
  5. customover crushed ice
  6. filtrationthe resulting precipitate was filtered
  7. washwashed with water
  8. filtrationthen filtered
  9. washwashed again with water affording 15.1 g (60%) of 5-methyl-6-nitro-4H-3,1-benzoxazin-2,4-dione
  10. customafter drying

출처 및 근거

ORD 기록
ord-a9fe05a4309c4334ab0e66bdbc3bce1c
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06380189B1

연결된 노트

불러오는 중…