Triethylamine → HCID 15426387, compound

HRID 842551Notes

Reaction equation

HRID 842551 reaction equation
[Cl:1][C:2]1[C:10]([CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(Cl)(=O)C(Cl)=O.[C:29]1(=O)[CH2:34][CH2:33][CH2:32][CH2:31][C:30]1=[O:35].C(N(CC)CC)C>CN(C)C=O.C(Cl)Cl>[Cl:1][C:2]1[C:10]([CH2:11][O:12][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:9]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:34]1[CH2:33][CH2:32][CH2:31][C:30](=[O:35])[CH:29]=1)=[O:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 130061,2-CyclohexanedioneHCID 65578Oxalyl chlorideHCID 22614273HCID 22614273, compound

Product 1

HCID 15426387HCID 15426387, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

0.53 g (1.53 mmol) of 2-chloro-3-cyclohexanyloxymethyl-4-methylsulfonylbenzoic acid was treated with 2 drops of N,N-dimethylformamide and 0.59 g (4.58 mmol) of oxalyl chloride in 23 ml of methylene chloride and the mixture was refluxed for 2.5 h. It was then stripped off on a rotary evaporator, the residue was taken up in 23 ml of methylene chloride and the mixture was treated at 0° C. with 0.19 g (1.68 mmol) of cyclohexanedione and 0.46 g (4.58 mmol) of triethylamine. It was stirred at room temperature for 4 h. It was then concentrated on a rotary evaporator and purified by chromatography (silica gel, ethyl acetate:hexane=1:1).

Workup

  1. temperaturethe mixture was refluxed for 2.5 h
  2. customIt was then stripped off on a rotary evaporator
  3. concentrationIt was then concentrated on a rotary evaporator
  4. custompurified by chromatography (silica gel, ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-e0890f92eccd48eab0ad056853376d64
Source dataset
uspto-grants-2002_04
Patent number
US06376429B1

Reaction notes

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