Triethylamine → HCID 19607536, compound

HRID 1602772Notes

Reaction equation

HRID 1602772 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]3[C:16]([CH3:17])=[C:15]([C:18]([OH:20])=[O:19])[CH:14]=[C:13]([CH3:21])[C:8]=3[S:9](=[O:12])(=[O:11])[CH2:10][C:5]=2[CH:4]=[N:3]1.C(Cl)(=O)C(Cl)=O.[C:28]1(=O)[CH2:33][CH2:32][CH2:31][C:30](=[O:34])[CH2:29]1.C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[CH3:1][N:2]1[C:6]2[C:7]3[C:16]([CH3:17])=[C:15]([C:18]([O:20][C:28]4[CH2:33][CH2:32][CH2:31][C:30](=[O:34])[CH:29]=4)=[O:19])[CH:14]=[C:13]([CH3:21])[C:8]=3[S:9](=[O:11])(=[O:12])[CH2:10][C:5]=2[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 104341,3-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 54491179HCID 54491179, compound

Product 1

HCID 19607536HCID 19607536, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2.0 g (0.0065 mol) of the title compound of Step B, 1.71 mL (0.0196 mol) of oxalyl chloride (purchase from Janssen), and 2 drops of N,N-dimethylformamide were added to 50 mL of methylene chloride. The mixture was refluxed under nitrogen for 2 h and was then evaporated to dryness. 50 mL of methylene chloride was added to the residue and it was then evaporated to dryness. Another 50 mL of methylene chloride was added to the residue and the solution was cooled to about 0° C. 0.80 g (0.0071 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 for 3 days while warming to room temperature. The mixture was evaporated to dryness and the crude product was chromatographed over silica gel eluting with a mixture of ethyl acetate:hexane (6:4) to yield 0.86 g of the title compound of Step C as a solid melting at 196° C. (decomposed). 1H NMR (CDCl3): δ2.2(m,2H), 2.5 (m,2H), 2.64 (s,3H), 2.7 (m,2H), 2.8 (s,3H), 3.8 (s,3H), 4.3 and 4.4 (2d, 2H), 6.06 (s,1H), 7.65 (s,1H), 7.94 (s,1H).

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 2 h
  2. customwas then evaporated to dryness
  3. addition50 mL of methylene chloride was added to the residue and it
  4. customwas then evaporated 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. customthe crude product was chromatographed over silica gel eluting with a mixture of ethyl acetate:hexane (6:4)

Sources & evidence

ORD record
ord-64240a557e9d482b97db5ad69c593075
Source dataset
uspto-grants-1999_11
Patent number
US05985799

Reaction notes

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