Triethylamine → HCID 19896880, compound

HRID 1196906Notes

Reaction equation

HRID 1196906 reaction equation
Cl[C:2](=[N:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=1)[C:3]([O:5][CH3:6])=[O:4].[CH:16]([C:18]1[O:19][CH:20]=[CH:21][CH:22]=1)=[CH2:17].C(N(CC)CC)C>C1C=CC=CC=1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]2[CH:16]([C:18]3[O:19][CH:20]=[CH:21][CH:22]=3)[CH2:17][C:2]([C:3]([O:5][CH3:6])=[O:4])=[N:7]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 738812-EthenylfuranHCID 71835133HCID 71835133, compound

Product 1

HCID 19896880HCID 19896880, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The compound of Example 1 (2.0 g) was suspended in benzene (20 ml) and heated to reflux in the presence of 2-vinylfuran (2.5 ml). Triethylamine was added and the mixture was allowed to reflux for 1 hour longer. The mixture was partitioned between water and ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and concentrated. Chromatography on silica gel (5:1 hexanes/ethyl acetate) gave the title compound (1.8 g). NMR (CDCl3) 7.3 to 6.9 (m, Ar-H, 5H); 6.2 (m, Furan-H, 2H); 5.5 (dd, CH, 1H); 3.9 (s, OCH3, 3H); 3.6 (m, CH, 1H); 3.4 (m, CH3, 1H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour longer
  3. customThe mixture was partitioned between water and ethyl acetate
  4. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c766592e2e0748db9d34f6ea3685c727
Source dataset
uspto-grants-1992_05
Patent number
US05116850

Reaction notes

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