Triethylamine → HCID 70201988, compound

HRID 378815Notes

Reaction equation

HRID 378815 reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH:13]2[C:22]3[C:17](=[C:18]([CH3:27])[CH:19]=[C:20]([C:24]([OH:26])=[O:25])[C:21]=3[CH3:23])[S:16](=[O:29])(=[O:28])[CH2:15][CH2:14]2)=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.C(Cl)(=O)C(Cl)=O.[C:36]1(=O)[CH2:41][CH2:40][CH2:39][CH2:38][C:37]1=[O:42].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[C:3]([O:12][CH:13]2[C:22]3[C:17](=[C:18]([CH3:27])[CH:19]=[C:20]([C:24]([O:26][C:41]4[CH2:40][CH2:39][CH2:38][C:37](=[O:42])[CH:36]=4)=[O:25])[C:21]=3[CH3:23])[S:16](=[O:28])(=[O:29])[CH2:15][CH2:14]2)=[N:4][CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 130061,2-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 70204223HCID 70204223, compound

Product 1

HCID 70201988HCID 70201988, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

0.56 g (1.2 mmol) of 4-{[3-chloro-5-(trifluoromethyl)-2-pyridyl]oxy}-5,8-dimethyl-1,1-dioxo-1,2,3,4-tetrahydro-1λ6-thiochromene-6-carboxylic acid in 30 ml of methylene chloride was admixed with 2 drops of N,N-dimethylformamide and 0.48 g (3.8 mmol) of oxalyl chloride, and the mixture was boiled under reflux for 3.5 h. The solvents were subsequently stripped off using a rotary evaporator and the residue was taken up in 100 ml of methylene chloride and, at 0° C., admixed with 0.15 g (1.4 mmol) of cyclohexanedione and 0.22 g (3.7 mmol) of triethylamine. The mixture was stirred at room temperature for 4 h and subsequently concentrated using a rotary evaporator, and the residue was purified by chromatography (silica gel, ethyl acetate: hexane=1:1).

Workup

  1. temperatureunder reflux for 3.5 h
  2. customa rotary evaporator
  3. customwas taken up in 100 ml of methylene chloride and, at 0° C.
  4. concentrationsubsequently concentrated
  5. customa rotary evaporator
  6. customthe residue was purified by chromatography (silica gel, ethyl acetate: hexane=1:1)

Sources & evidence

ORD record
ord-0ea70d5563ef48a79335199422a5c8e7
Source dataset
uspto-grants-2001_10
Patent number
US06297196B1

Reaction notes

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