Hydrochloric Acid → 2-(5-Methoxy-2-methyl-4-nitrophenyl)acetonitrile

HRID 354063

반응식

HRID 354063 반응식
[OH-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([N+:12]([O-:14])=[O:13])[CH:5]=1.C1(S[CH2:22][C:23]#[N:24])C=CC=CC=1.Cl>CS(C)=O>[CH3:11][O:10][C:7]1[C:6]([N+:12]([O-:14])=[O:13])=[CH:5][C:4]([CH3:3])=[C:9]([CH2:22][C:23]#[N:24])[CH:8]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 670581-Methoxy-4-methyl-2-nitrobenzeneHCID 78891(Phenylthio)acetonitrile

생성물 1

HCID 235129902-(5-Methoxy-2-methyl-4-nitrophenyl)acetonitrile수율 81%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To a suspension of powdered sodium hydroxide (5.76 g, 144.0 mmol) in anhydrous dimethylsulfoxide (14 mL) was added a mixture of 4-methyl-2-nitro-anisole (2.0 mL, 14.4 mmole) and phenylthioacetonitrile (1.88 mL, 14.4 mmole) in anhydrous dimethylsulfoxide (14 mL). The reaction mixture was kept under 30° C. After stirring for one hour at room temperature, the reaction mixture was poured into ice water (400 mL) and 6N hydrochloric acid (40 mL). The mixture was extracted with dichloromethane. The organic layer was washed with water, dried (anhydrous magnesium sulfate), filtered and concentrated under reduced pressure. The resulting solid was washed with a small amount of hexanes and a small amount of ethyl acetate to give (5-methoxy-2-methyl-4-nitro-phenyl)-acetonitrile as a solid (2.40 g, 81%). 1H NMR (CDCl3) δ: 2.32 (s, 3H), 3.73 (s, 2H), 3.99 (s, 3H), 7.15 (s, 1H), 7.73 (s, 1H).

후처리

  1. additionwas added
  2. customwas kept under 30° C
  3. extractionThe mixture was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting solid was washed with a small amount of hexanes

출처 및 근거

ORD 기록
ord-a2500a455afe48c48371c3458de6ef8c
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756395B2

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