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

HRID 351562

反応式

HRID 351562 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e22c4e17d82f4d52a1b42abd2bf3c54c
出典データセット
uspto-grants-2004_06
特許番号
US06743792B2

関連ノート

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