Triethylamine → HCID 70201865, compound

HRID 378817Notes

Reaction equation

HRID 378817 reaction equation
[C:1]([O:9][CH:10]1[C:19]2[C:14](=[C:15]([CH3:24])[CH:16]=[C:17]([C:21]([OH:23])=[O:22])[C:18]=2[CH3:20])[S:13](=[O:26])(=[O:25])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[C:33]1(=O)[CH2:38][CH2:37][CH2:36][CH2:35][C:34]1=[O:39].C(N(CC)CC)C>C(Cl)Cl.CN(C)C=O>[C:1]([O:9][CH:10]1[C:19]2[C:14](=[C:15]([CH3:24])[CH:16]=[C:17]([C:21]([O:23][C:38]3[CH2:37][CH2:36][CH2:35][C:34](=[O:39])[CH:33]=3)=[O:22])[C:18]=2[CH3:20])[S:13](=[O:25])(=[O:26])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 130061,2-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 70204619HCID 70204619, compound

Product 1

HCID 70201865HCID 70201865, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

0.80 g (2.1 mmol) of 4-benzoyloxy-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 1.69 g (13.3 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 0.25 g (2.2 mmol) of cyclohexanedione and 0.44 g (7.4 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-79ac26229f9a4152abeb14c3e63cf6f7
Source dataset
uspto-grants-2001_10
Patent number
US06297196B1

Reaction notes

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