Sodium Hydroxide → 1-(Cyclohexylmethyl)-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

HRID 276294

반응식

HRID 276294 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]=[C:12]1[S:16][CH2:15][C:14]2([CH2:20][CH2:19][CH2:18][CH2:17]2)[NH:13]1.Br[CH2:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-].[Na+]>CN(C=O)C>[CH:23]1([CH2:22][N:13]2[C:14]3([CH2:17][CH2:18][CH2:19][CH2:20]3)[CH2:15][S:16][C:12]2=[N:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[CH3:1])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 137636Cyclohexane, (bromomethyl)-HCID 1784287362-(2-Methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane

생성물 1

HCID 183160771-(Cyclohexylmethyl)-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane수율 32%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
45 °C

실험 절차

To a solution of 2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (Method C2a; 0.10g, 0.3432 mmol) and bromomethylcyclohexane (1.00 mL) in DMF (1.00 mL) was added NaOH (approx. 0.13 g). The resulting mixture was stirred at 45° C. for 2 d during which it turned from deep red to bright orange. The reaction mixture was then cooled to room temp., filtered and concentrated under reduced pressure. The residual oil was purified by chromatography (SiO2; 5% EtOAc/hex) to afford 1-(cyclohexylmethyl)-2-(2-methyl-4-nitrophenylimino)-3-thia-1-azaspiro[4.4]nonane (0.042 g, 32%) mp 85-7° C.

후처리

  1. temperatureThe reaction mixture was then cooled to room temp.
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customThe residual oil was purified by chromatography (SiO2; 5% EtOAc/hex)

출처 및 근거

ORD 기록
ord-9be90650ac23408a99f66696544e0098
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06353006B1

연결된 노트

불러오는 중…