Water → 2-(1-Bromo-ethyl)-6-methanesulfonyl-3-methyl-3H-quinazolin-4-one

HRID 238207노트

반응식

HRID 238207 반응식
[CH2:1]([C:3]1[N:12]([CH3:13])[C:11](=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:15]([CH3:18])(=[O:17])=[O:16])[CH:9]=2)[N:4]=1)[CH3:2].[Br:19]Br.O>C(O)(=O)C>[Br:19][CH:1]([C:3]1[N:12]([CH3:13])[C:11](=[O:14])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([S:15]([CH3:18])(=[O:16])=[O:17])[CH:9]=2)[N:4]=1)[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 24408BromineHCID 599934672-Ethyl-6-methanesulfonyl-3-methyl-3H-quinazolin-4-one

생성물 1

HCID 599932062-(1-Bromo-ethyl)-6-methanesulfonyl-3-methyl-3H-quinazolin-4-one수율 87.2%

시약·촉매·용매 1

HCID 176Acetic Acid용매3회

실험 절차

To a solution 2-ethyl-6-methanesulfonyl-3-methyl-3H-quinazolin-4-one (300.0 mg, 1.13 mmol) in glacial acetic acid (10 ml) cooled in an ice bath was added dropwise a solution of bromine (0.39 g, 2.26 mmol) in glacial acetic acid (5 ml). After addition was complete, the reaction was heated to reflux for 18 hours. Evaporated acetic acid and then water was added to the solution and the mixture was extracted with dichloromethane. The organic layer was washed with 10% sodium bisulfite solution, and then washed with saturated brine (2×10 ml). The combined organic phase was collected and dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield a brown crude product. The resulting residue was purified by silica gel chromatography with 50% ethyl acetate in hexane. The product was collected and was dried under reduced pressure to give 2-(1-Bromo-ethyl)-6-methanesulfonyl-3-methyl-3H-quinazolin-4-one (Yield 339 mg, 87.2%). 1H NMR (400 MHz, CDCl3): δ 2.13 (d, 3H, J=5.31 Hz), 3.04 (s, 3H), 3.71 (s, 3H), 5.05 (m, 1H), 7.81 (d, 1H, J=7.58 Hz), 8.16 (d, 1H, J=7.58, Hz), 8.80 (s, 1H). MS m/z calc. 343.98, found (ESI); 344.8 (M+1)+. Retention time 3.06 minutes.

후처리

  1. additionAfter addition
  2. temperaturethe reaction was heated
  3. temperatureto reflux for 18 hours
  4. extractionthe mixture was extracted with dichloromethane
  5. washThe organic layer was washed with 10% sodium bisulfite solution
  6. washwashed with saturated brine (2×10 ml)
  7. customThe combined organic phase was collected
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto yield a brown crude product
  12. customThe resulting residue was purified by silica gel chromatography with 50% ethyl acetate in hexane
  13. customThe product was collected
  14. customwas dried under reduced pressure

출처 및 근거

ORD 기록
ord-df83d1f3d92e4d27a4869c41dccc0c2c
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642609B2

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