1,3-Cyclohexanedione → HCID 69916322, compound

HRID 2306540Notes

Reaction equation

HRID 2306540 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:9]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:23]1(=O)[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH2:24]1.Cl.CN(C)CCCN=C=NCC.CN(C1C=CC=CN=1)C>C(Cl)Cl>[Cl:1][C:2]1[C:10]([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[C:9]([S:18]([CH2:21][CH3:22])(=[O:20])=[O:19])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:23]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH:24]=1)=[O:5]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 218852-DimethylaminopyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15906663HCID 15906663, compound

Product 1

HCID 69916322HCID 69916322, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.550 g (1.60 mmol) of 2-chloro-3-cyclopentylmethoxy-4-ethylsulfonylbenzoic acid, 0.196 g (1.70 mmol) of cyclohexane-1,3-dione, 0.279 g (1.40 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 0.002 g of dimethylaminopyridine were stirred for 10 hours at room temperature in 15 ml of methylene chloride. The mixture was subsequently diluted with methylene chloride and washed with 0.5 N HCl, with water, with saturated NaHCO3 solution and again with water. After the combined organic phases had been dried over Na2SO4 and evaporated completely on a rotary evaporator, 3-oxo-1-cyclohexenyl 2-chloro-3-cyclopentylmethoxy-4-ethylsulfonylbenzoate was obtained in the form of a brown resin.

Workup

  1. washwashed with 0.5 N HCl, with water, with saturated NaHCO3 solution and again with water
  2. dry with materialAfter the combined organic phases had been dried over Na2SO4
  3. customevaporated completely on a rotary evaporator

Sources & evidence

ORD record
ord-176454e7462b4c418160bf0f9b191105
Source dataset
uspto-grants-2004_12
Patent number
US06828276B2

Reaction notes

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