Water → (+/-)-2,6-Dichloro-alpha-methyl4-nitrobenzeneacetonitrile

HRID 1072484ノート

反応式

HRID 1072484 の反応式
BrC1CC[O:4]C1=O.[Cl:8][C:9]1[CH:14]=[C:13]([N:15]2C(=O)NC(=O)C=N2)[CH:12]=[C:11](Cl)[C:10]=1[C:24]([C:27]1SC(CC(O)=O)=C(C2C=CC=CC=2)[N:31]=1)(C)[CH3:25].C([O-])(O)=O.[Na+].[Na+].[Cl-:48].[OH2:49]>CN(C=O)C>[Cl:48][C:11]1[CH:12]=[C:13]([N+:15]([O-:4])=[O:49])[CH:14]=[C:9]([Cl:8])[C:10]=1[CH:24]([CH3:25])[C:27]#[N:31]

参加物

7

反応物 5

HCID 962WaterHCID 5234Sodium ChlorideHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 516892Sodium BicarbonateHCID 158708342-[1-[2,6-dichloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)yl)phenyl]-1-methylethyl]-4-phenyl-5-thiazoleacetic acid

生成物 1

HCID 22386574(+/-)-2,6-Dichloro-alpha-methyl4-nitrobenzeneacetonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
70 °C

実験手順

A mixture of 3-bromodihydro-2(3H)-furanone (0.0081 mole) in DMF (16 ml) was added dropwise at room temperature to a mixture of intermediate (10)(0.00773 mole) and NaHCO3 (0.0081 mole) in DMF (30 ml). The mixture was stirred at 70° C. for 5 hours and brought to room temperature. H2O and a saturated NaCl solution were added. The mixture was extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue (5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15-40 μm). The pure fractions were collected and the solvent was evaporated. The residue was taken up in DIPE. The precipitate was filtered off and dried, yielding 1.24 g of compound 1 having a melting point of 72° C. and represented by the formula

後処理

  1. custombrought to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15-40 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated
  10. filtrationThe precipitate was filtered off
  11. customdried

出典と根拠

ORDレコード
ord-8cef754375a1416ba2fe883e3b397625
出典データセット
uspto-grants-2005_06
特許番号
US06911444B2

反応ノート

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