Imidazole → (S)-4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

HRID 1191376노트

반응식

HRID 1191376 반응식
O[CH2:2][C@@H:3]([CH3:17])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N1C=CN=C1.[I:42]I>C(Cl)Cl>[I:42][CH2:2][C@@H:3]([CH3:17])[CH2:4][N:5]1[C:10]2[CH:11]=[C:12]([CH3:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]1=[O:16]

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 68908602(S)-4-(3-Hydroxy-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one

생성물 1

HCID 68908548(S)-4-(3-iodo-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one수율 103.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A dry 50 mL r-flask was charged with (S)-4-(3-hydroxy-2-methylpropyl)-6-methyl-4H-benzo[1,4]oxazin-3-one (1.0 g, 4.2 mmol), PPh3 (2.2 g, 8.5 mmol), imidazole (0.58 g, 8.5 mmol) and dissolved with CH2Cl2 (25 mL). Iodine (2.2 g, 8.4 mmol) was then added in small portions over 4 h period. After the last addition the reaction was poured onto SiO2 and filtered. Concentration under reduced pressure yielded the crude title compound (1.5 g), which was used without further purification.

후처리

  1. additionAfter the last addition the reaction
  2. additionwas poured onto SiO2
  3. filtrationfiltered
  4. concentrationConcentration under reduced pressure

출처 및 근거

ORD 기록
ord-7edadfc7f46943ab9942b5c94e726719
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680115B2

반응 노트

불러오는 중…