1,2-Dichloroethane → HCID 20356415, compound

HRID 371754Notes

Reaction equation

HRID 371754 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]([CH2:13][CH:14]([CH3:16])[CH3:15])[CH3:12])=[CH:6][CH:5]=1)[CH3:2].II.C(Cl)CCl.[CH3:23][C:24]([CH3:26])=O>>[CH3:12][C:11]1([CH2:13][CH:14]([CH3:15])[CH3:16])[CH:23]=[C:24]([CH3:26])[C:8]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH2:1][CH3:2])[CH:9]=2)[NH:10]1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 180AcetoneHCID 807IodineHCID 7136984366053-09-6

Product 1

HCID 20356415HCID 20356415, compound

Procedure

A portion (5.98g) of this material, 4-methyl-2-pentanone p-ethoxyphenylimine, combined with iodine (0.15g), ethylene dichloride (0.5 ml) and acetone (200 ml), was refluxed for about 26 hours in a Soxhlet extractor, which was charged with molecular sieves 3A and fitted with a moisture trap at the condenser outlet. The product was evaporated to dryness in vacuo and then fractionated. Fractions with b.p.≥120° C/0.5 mm were combined and the brown oil (3.26lg) was chromatographed on silica gel (180g, mesh 70-230). Benzene (2 l.) and benzene-chloroform (9:1, 1.5 l.) eluates furnished 1,2-dihydro-2,4-dimethyl-2-isobutyl-6-ethoxyquinoline as a brown oil (1.88g).

Workup

  1. temperaturewas refluxed for about 26 hours in a Soxhlet extractor, which
  2. customfitted with a moisture trap at the condenser outlet
  3. customThe product was evaporated to dryness in vacuo
  4. customthe brown oil (3.26lg) was chromatographed on silica gel (180g, mesh 70-230)

Sources & evidence

ORD record
ord-4f8153c5195140b093162dff4a21b12c
Source dataset
uspto-grants-1978_05
Patent number
US04087561

Reaction notes

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