Triethylamine → HCID 19047186, compound

HRID 1780597Notes

Reaction equation

HRID 1780597 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][S:6](=[O:14])(=[O:13])[C:5]=2[S:4][C:3]=1[C:15]([OH:17])=[O:16].C(Cl)(=O)C(Cl)=O.[C:24]1(=O)[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH2:25]1.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[CH3:1][C:2]1[C:10]2[C:9]([CH3:12])([CH3:11])[CH2:8][CH2:7][S:6](=[O:13])(=[O:14])[C:5]=2[S:4][C:3]=1[C:15]([O:17][C:24]1[CH2:29][CH2:28][CH2:27][C:26](=[O:30])[CH:25]=1)=[O:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 67712506HCID 67712506, compound

Product 1

HCID 19047186HCID 19047186, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g (0.0073 mol) of the title compound of Step D was added to 50 mL of methylene chloride. 1.27 mL (0.0146 mol) of oxalyl chloride (purchased from Janssen) was added followed by 2 drops of N,N-dimethylformamide. The mixture was refluxed under nitrogen for 2 h and then was evaporated to dryness. 50 mL of methylene chloride was added to the residue and then evaporated to dryness. Another 50 mL of methylene chloride was added to the residue and the solution was cooled to about 0° C. 0.90 g (0.0080 mol) of 1,3-cyclohexanedione (purchased from Aldrich Chemical Company) was added followed by 2.8 mL (0.020 mol) of triethylamine, and the mixture was stirred overnight while warming to room temperature. The mixture was evaporated to dryness, the residue was stirred in 100 mL of water and filtered. The crude product was washed with hexane to yield 2.32 g of the title compound of Step E as a solid melting at 133°-134° C. 1H NMR (CDCl3): δ 1.48 (s,6H), 2.1 (m,2H), 2.4 (m,4H), 2.6 (m,2H), 2.7 (s,3H), 3.4 (m,2H), 6.06 (s,1H).

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 2 h
  2. customwas evaporated to dryness
  3. addition50 mL of methylene chloride was added to the residue
  4. customevaporated to dryness
  5. additionAnother 50 mL of methylene chloride was added to the residue
  6. temperaturewhile warming to room temperature
  7. customThe mixture was evaporated to dryness
  8. stirringthe residue was stirred in 100 mL of water
  9. filtrationfiltered
  10. washThe crude product was washed with hexane

Sources & evidence

ORD record
ord-c93628bb988b4d62be76321cbd23456b
Source dataset
uspto-grants-1997_05
Patent number
US05631210

Reaction notes

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