HCID 136486663, compound → HCID 20291380, compound

HRID 1863428Notes

Reaction equation

HRID 1863428 reaction equation
C[O:2][C:3](=O)[NH:4][N:5]=[C:6]([C:8]1[N:9]=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:11][C:12]=1[I:13])C>ClC1C=CC=CC=1Cl.CO>[C:14]1([C:10]2[N:9]3[C:3](=[O:2])[NH:4][N:5]=[CH:6][C:8]3=[C:12]([I:13])[N:11]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 136486663HCID 136486663, compound

Product 1

HCID 20291380HCID 20291380, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 72391,2-DichlorobenzeneSolvent

Procedure

3-[1-(5-Iodo-2-phenyl-4-imidazolyl)ethylidene]-carbazic acid methyl ester (1.01 gm., 0.0027 mole) is dissolved in a mixture of o-dichlorobenzene (150 ml.) and methanol (15 ml.). The solution is heated to the boiling point and boiled for 20 minutes allowing solvent to distill off partially. The reaction mixture is chromatographed over a silica gel column and eluted with a hexane-ethyl acetate (2:1) mixture to yield the title product (0.63 gm., 0.0019 mole). Recrystallization from ethyl acetate-hexane yields the product as yellow needles, m.p. 176°-189° C.

Workup

  1. temperatureThe solution is heated to the boiling point
  2. distillationto distill off partially
  3. customThe reaction mixture is chromatographed over a silica gel column
  4. washeluted with a hexane-ethyl acetate (2:1) mixture

Sources & evidence

ORD record
ord-46c13dd466774a7abe5e1209d538804f
Source dataset
uspto-grants-1979_09
Patent number
US04168964

Reaction notes

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