Chloroform → HCID 14328883, compound

HRID 867960

Reaction equation

HRID 867960 reaction equation
[N:1]1([CH2:6][C:7]([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)=[N+:8]([O-:10])[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:21]([O:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[CH:22]=[CH2:23].C(Cl)(Cl)Cl>C1(C)C=CC=CC=1>[N:1]1([CH2:6][C:7]2([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH:12]=3)[CH2:23][CH:22]([CH2:21][O:24][C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)[O:10][N:8]2[CH3:9])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 2886701-Allyloxy-4-methoxybenzeneHCID 867424722-(1H-Imidazol-1-yl)-N-methyl-1-(2-naphthalenyl)ethanimine N-oxide

Product 1

HCID 14328883HCID 14328883, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of compound 2 (13.0 g, 0.049 mol) and p-methoxyphenyl allyl ether (12.07 g, 0.073 mol) in 400 ml of toluene is refluxed for 48 hours, cooled, and the solvent removed in vacuo leaving a dark oil. Chloroform is added to the oil and carbon is added to decolorize the solution which is filtered through a bed of celite. The chloroform is evaporated and the oil that remained is purified by flash chromatography on silica gel (eluent comprised of 98% CHCl3 and 2% MeOH). The resulting tan solid (5.56 g, 26%) is recrystallized from ethyl acetate, m.p. 143°-145° C. (Found: C, 72.58; H, 6.46; N, 9.66. C26H27N3O3 requires: C, 72.71; H, 6.34; N, 9.78).

Workup

  1. temperatureis refluxed for 48 hours
  2. temperaturecooled
  3. customthe solvent removed in vacuo
  4. customleaving a dark oil
  5. additionis added
  6. filtrationis filtered through a bed of celite
  7. customThe chloroform is evaporated
  8. customthe oil that remained is purified by flash chromatography on silica gel (eluent comprised of 98% CHCl3 and 2% MeOH)
  9. customThe resulting tan solid (5.56 g, 26%) is recrystallized from ethyl acetate, m.p. 143°-145° C. (Found: C, 72.58; H, 6.46; N, 9.66. C26H27N3O3 requires: C, 72.71; H, 6.34; N, 9.78)

Sources & evidence

ORD record
ord-ec5a6d3cf0aa48b2a5dc44b008f874d4
Source dataset
uspto-grants-1988_10
Patent number
US04777263

Linked notes

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