Water → (+/-)-2,6-Dichloro-alpha-methyl4-nitrobenzeneacetonitrile
Reaction equation
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]Participants
Conditions
- Temperature
- 70 °C
Procedure
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
Workup
- custombrought to room temperature
- extractionThe mixture was extracted with EtOAc
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- filtrationfiltered
- customthe solvent was evaporated
- customThe residue (5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 98/2; 15-40 μm)
- customThe pure fractions were collected
- customthe solvent was evaporated
- filtrationThe precipitate was filtered off
- customdried
Sources & evidence
- ORD record
- ord-8cef754375a1416ba2fe883e3b397625
- Source dataset
- uspto-grants-2005_06
- Patent number
- US06911444B2
Reaction notes
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