Hantzsch ester → HCID 22617822, compound

HRID 841900Notes

Reaction equation

HRID 841900 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH:13]=[C:12]2[CH:26]=[C:27]1[S:31][C:30](=[O:32])[NH:29][C:28]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC1NC(C)=C(C(OCC)=O)CC=1C(OCC)=O>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=1)[CH:13]=[C:12]2[CH2:26][CH:27]1[S:31][C:30](=[O:32])[NH:29][C:28]1=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70849Hantzsch esterHCID 131723183HCID 131723183, compound

Product 1

HCID 22617822HCID 22617822, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To oven-dried SiO2(150 mg) in toluene (2 mL) was added 50 mg of the thiazolidinylidene olefin (Example 1) with diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate (25 mg). The mixture was stirred and heated at 70-90° for 3 days. Mass spectral monitoring indicated the reaction was complete. Silica was filtered and washed with EtOAc and combined volatiles were removed under reduced pressure to a residue. The solid dissolved in ether and solids were filtered and discarded. Ether was evaporated and residue was washed with hexanes and air-dried to afford the reduction product; ms: m/e 512 (M+1); HPLC ˜70% pure.

Workup

  1. temperatureheated at 70-90° for 3 days
  2. filtrationSilica was filtered
  3. washwashed with EtOAc
  4. customwere removed under reduced pressure to a residue
  5. dissolutionThe solid dissolved in ether
  6. filtrationsolids were filtered
  7. customEther was evaporated
  8. washresidue was washed with hexanes
  9. customair-dried
  10. customto afford the reduction product

Sources & evidence

ORD record
ord-09d43a84fc35425e9cadc5b00205d300
Source dataset
uspto-grants-2002_04
Patent number
US06372742B1

Reaction notes

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