Benzene → HCID 19908446, compound

HRID 1534862Notes

Reaction equation

HRID 1534862 reaction equation
Cl[C:2](=[N:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C1C=CC=CC=1.[Cl:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[CH2:29])=[CH:26][CH:25]=1>C(N(CC)CC)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([N:9]2[CH:28]([C:27]3[CH:30]=[CH:31][C:24]([Cl:23])=[CH:25][CH:26]=3)[CH2:29][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[N:8]2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 241Benzene2×HCID 140854-ChlorostyreneHCID 2761323Ethyl 2-chloro-2-(2-(4-chlorophenyl)hydrazono)acetate

Product 1

HCID 19908446HCID 19908446, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

The compound of Example 6 (5.0 gm) was heated in refluxing benzene (30 ml) containing 4-chlorostyrene (7.0 ml). Addition of a benzene (10 ml) solution of triethylamine(7.5 ml) was followed by one hour of continued heating. The cooled mixture was filtered, rotovapped, and dried on the vacuum pump to remove excess styrene. The residual solid was recrystallized from hexane/benzene (charcoal) to give the title compound (6.3 gm); m.p.: 128° to 130° C. NMR (CDCl3) 7.3-6.9 (m, 8H, ArH), 5.4 (dd, 1H, CH), 4.3 (q, 2H, OCH2), 3.8 (m, 1H, CH), 3.0 (m, 1H, CH), 1.38 (t, 3H, CH3).

Workup

  1. filtrationThe cooled mixture was filtered
  2. customdried on the vacuum pump
  3. customto remove excess styrene
  4. customThe residual solid was recrystallized from hexane/benzene (charcoal)

Sources & evidence

ORD record
ord-0eaccc472e414ffea3686fdd4b1946cb
Source dataset
uspto-grants-1992_02
Patent number
US05091405

Reaction notes

Loading…