1,3-Cyclohexanedione → HCID 22340629, compound

HRID 585324Notes

Reaction equation

HRID 585324 reaction equation
[Cl:1][C:2]1[C:10]([O:11][CH2:12][C:13]([CH3:15])=[O:14])=[C:9]([S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:21]1(=O)[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH2:22]1.Cl.CN(C)CCCN=C=NCC.CC1C=CN=C(N)C=1C>C(Cl)Cl>[Cl:1][C:2]1[C:10]([O:11][CH2:12][C:13]([CH3:15])=[O:14])=[C:9]([S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:21]1[CH2:26][CH2:25][CH2:24][C:23](=[O:27])[CH:22]=1)=[O:5]

Participants

6

Reactant 4

HCID 104341,3-CyclohexanedioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110078842-Amino-3,4-dimethylpyridineHCID 22340628HCID 22340628, compound

Product 1

HCID 22340629HCID 22340629, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.295 g (0.9 mmol) of 2-chloro-3-(methylcarbonylmethoxy)-4-ethylsulfonylbenzoic acid, 0.113 g (1.0 mmol) of cyclohexane-1,3-dione, 0.180 g (0.9 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride and 0.001 g of dimethyl-aminopyridine were stirred in 25 ml of CH2Cl2 at RT for 2 h. The mixture was then diluted with CH2Cl2 and washed with 0.5 N HCl, with water, with saturated NaHCO3 solution and again with water. The combined organic phases were dried over Na2SO4 and then evaporated to dryness, giving 3-oxo-1-cyclohexenyl 2-chloro-3-(methylcarbonylmethoxy)-4-ethylsulfonylbenzoate in the form of a brown resin which was sufficiently pure for the subsequent reaction.

Workup

  1. washwashed with 0.5 N HCl, with water, with saturated NaHCO3 solution and again with water
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-09a04ad39724402a9226e6fcd90b4c7b
Source dataset
uspto-grants-2005_08
Patent number
US06930208B2

Reaction notes

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