Triethylamine → HCID 20183856, compound

HRID 255655Notes

Reaction equation

HRID 255655 reaction equation
[C:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]([C:20]3[S:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[CH:21]=3)=[CH:18][C:17](=[O:29])[C:13]([C:14]([OH:16])=[O:15])=[CH:12]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:43]1[C:51]2[C:46](=[CH:47][C:48](O)=[CH:49][CH:50]=2)[CH2:45][CH2:44]1>C(Cl)Cl>[C:1]([O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:19]([C:20]3[S:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[CH:21]=3)=[CH:18][C:17](=[O:29])[C:13]([C:14]([O:16][CH:43]3[C:51]4[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=4)[CH2:45][CH2:44]3)=[O:15])=[CH:12]2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 151185-IndanolHCID 20183834HCID 20183834, compound

Product 1

HCID 20183856HCID 20183856, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

In 18 ml of anhydrous methylene chloride was dissolved 0.36 g of 1-(4-acetoxyphenyl)-6-(2-benzo[b]thienyl)-4-oxo-1,4-dihydronicotinic acid, and to this solution was added 0.137 ml of triethylamine at room temperature. The reaction mixture thus obtained was cooled to -40° C., and 0.094 ml of ethyl chlorocarbonate was added thereto. The resulting mixture was subjected to reaction at the same temperature for 1 hour. This reaction mixture was then mixed with 0.14 g of 5-indanol. The mixture was subjected to reaction for 1 hour, and elevated to room temperature. After completion of the reaction, the reaction mixture was washed successively with 15 ml of water and a saturated aqueous solution of sodium chloride, and then dried with anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform) to obtain 0.25 g of indanyl 1-(4-acetoxyphenyl)-6-(2-benzo[b]thienyl)-4 -oxo-1,4-dihydronicotinate having a melting point of 234°-236° C.

Workup

  1. customThe reaction mixture thus obtained
  2. customThe resulting mixture was subjected to reaction at the same temperature for 1 hour
  3. customThe mixture was subjected to reaction for 1 hour
  4. customelevated to room temperature
  5. customAfter completion of the reaction
  6. washthe reaction mixture was washed successively with 15 ml of water
  7. dry with materiala saturated aqueous solution of sodium chloride, and then dried with anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customthe residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform)

Sources & evidence

ORD record
ord-4984c1d86e414d848afc56c7c5bf049d
Source dataset
uspto-grants-1987_10
Patent number
US04698352

Reaction notes

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