Dimethylformamide → HCID 22141260, compound

HRID 428910Notes

Reaction equation

HRID 428910 reaction equation
Cl[CH2:2][CH:3]1[CH:5]([C:6]([O:8]CC)=O)[C:4]1([CH2:20][CH3:21])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=1.C(=O)([O-])O.[Na+].C[N:28]([CH3:31])C=O>>[CH2:20]([C:4]1([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[CH:5]2[CH:3]1[CH2:2][N:28]([CH2:31][CH2:3][CH2:4][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]2=[O:8])[CH3:21]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 22141267HCID 22141267, compound

Product 1

HCID 22141260HCID 22141260, compound

Conditions

Temperature
150 °C

Procedure

To a solution of ethyl 3-(chloromethyl)-2-ethyl-2-(3-nitrophenyl)cyclopropane carboxylate (Preparation 16, 3.5 g, 11.2 mmol), in N,N-dimethylformamide (33 ml) was added sodium hydrogen carbonate (3.3 g, 39 mmol) and 3-phenylpropylamnine (10.6 g, 11.2 ml, 79.2 mmol). The mixture was heated to 150° C. for 12 h, then cooled to room temperature and partitioned between water (500 ml) and diethyl ether (500 ml). The organic layer was washed successively with water (4×250 ml). The aqueous layers were combined and extracted with diethyl ether (250 ml). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by silica (200 g) column chromatography eluting with dichloromethane. Product-containing fractions were combined and concentrated in vacuo to give the title compound as a very pale yellow oil (1.8 g, 43%).

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between water (500 ml) and diethyl ether (500 ml)
  3. washThe organic layer was washed successively with water (4×250 ml)
  4. extractionextracted with diethyl ether (250 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica (200 g) column chromatography
  9. washeluting with dichloromethane
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a0e06cf762248e38267a1e9e3979cae
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

Loading…