Benzoyl Peroxide → 6-bromo-2-methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one

HRID 1289221

반응식

HRID 1289221 반응식
[CH3:1][C:2]1[N:11]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:18])([CH3:17])[CH3:16])[C:10](=[O:20])[C:9]2[C:4](=[CH:5][C:6]3[CH2:23][CH2:22][CH2:21][C:7]=3[CH:8]=2)[N:3]=1.[Br:24]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:24][CH:21]1[C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][C:6]=2[CH2:23][CH2:22]1)[N:3]=[C:2]([CH3:1])[N:11]([CH2:12][O:13][C:14](=[O:19])[C:15]([CH3:16])([CH3:17])[CH3:18])[C:10]3=[O:20]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 108527582-Methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one

생성물 1

HCID 105246016-bromo-2-methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

반응 조건

온도
0 °C

실험 절차

A mixture of 2-methyl-3-pivaloyloxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]-quinazolin-4-one (50 g), N-bromosuccinimide (31.2 g), benzoyl peroxide (0.1 g) and carbon tetrachloride (500 ml) was stirred and heated to reflux for 90 minutes. The mixture was cooled to 0° C. The mixture was filtered and the filtrate was evaporated. The residue was triturated under diethyl ether (400 ml). The mixture was cooled to 0° C. The precipitate was isolated, washed with diethyl ether and dried. The solid so obtained was purified by column chromatography using a 1:1 mixture of hexane and ethyl acetate as eluant. There was thus obtained 6-bromo-2-methyl-3-pivaloyloxy-methyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-4-one (21 g), m.p. 98° C. (decomposes);

후처리

  1. temperatureheated
  2. temperatureto reflux for 90 minutes
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customThe residue was triturated under diethyl ether (400 ml)
  6. temperatureThe mixture was cooled to 0° C
  7. customThe precipitate was isolated
  8. washwashed with diethyl ether
  9. customdried
  10. customThe solid so obtained
  11. customwas purified by column chromatography
  12. additiona 1:1 mixture of hexane and ethyl acetate as eluant

출처 및 근거

ORD 기록
ord-543f7d44fbc94764a3bb4c39c3f6f95d
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05747499

연결된 노트

불러오는 중…