Hydrochloric Acid → (+/-)-alpha-(3,4-Dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrile

HRID 965636

반응식

HRID 965636 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[H-].[Na+].CO[C:16]1[C:21]([CH3:22])=[CH:20][C:19]([N+:23]([O-:25])=[O:24])=[CH:18][C:17]=1[CH3:26].Cl>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:16]2[C:17]([CH3:26])=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[CH:20][C:21]=2[CH3:22])[C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 76690(3,4-Dichlorophenyl)acetonitrileHCID 1398352-Methoxy-1,3-dimethyl-5-nitrobenzene

생성물 1

HCID 22312926(+/-)-alpha-(3,4-Dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrile수율 87%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

반응 조건

온도
0 °C

실험 절차

A mixture of (3,4-dichlorophenyl)acetonitrile (0.149 mol) in DMF (100 ml) was stirred at 0° C. under N2 flow. Sodium hydride (0.223 mol) was added portionwise. The mixture was stirred at 0° C. under N2 flow for 1 hour. A mixture of, 2-methoxy-1,3-dimethyl-5-nitrobenzene (0.149 mol) in DMF (100 ml) was added dropwise at 0° C. under N2 flow. The mixture was stirred at RT for 6 hours, then cooled, hydrolized with H2O and with HCl 3N and extracted with EtOAc. The organic layer was separated, washed several times with H2O, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE. The precipitate was filtered off and dried, yielding 43.4 g (87%) of (±)-α-(3,4-dichlorophenyl)-2,6-dimethyl-4-nitrobenzeneacetonitrile (interm. 48).

후처리

  1. stirringThe mixture was stirred at 0° C. under N2 flow for 1 hour
  2. additionwas added dropwise at 0° C. under N2 flow
  3. stirringThe mixture was stirred at RT for 6 hours
  4. extractionextracted with EtOAc
  5. customThe organic layer was separated
  6. washwashed several times with H2O
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was crystallized from DIPE
  11. filtrationThe precipitate was filtered off
  12. customdried

출처 및 근거

ORD 기록
ord-d08b914b289c4b42965af605431dc2e3
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06951857B2

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