1,3-Cyclohexanedione → HCID 67041881, compound

HRID 1929290Notes

Reaction equation

HRID 1929290 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1[NH:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17].[C:20]1(=O)[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH2:21]1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][C:20]2[CH2:25][CH2:24][CH2:23][C:22](=[O:26])[CH:21]=2)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[C:3]=1[NH:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67042000HCID 67042000, compound

Product 1

HCID 67041881HCID 67041881, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

190 mg (0.574 mmol) of 4-bromo-3-[(2,2-dimethylpropyl)amino]-2-nitrobenzoic acid, 198 mg (1.713 mmol) of cyclohexane-1,3-dione, 145 mg (0.741 mmol) of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride and 7 mg (0.057 mmol) of 4-(dimethylamino)pyridine were dissolved in 5 ml of methylene dichloride and stirred at RT for 24 h. The solution was then washed with water and saturated NaHCO3 solution, the organic phase was dried over MgSO4, and then the whole was filtered with suction through a glass frit, filled with 1 cm of silica gel, and the filter product was washed with heptane/ethyl acetate 1:2. The filtrate was concentrated.

Workup

  1. washThe solution was then washed with water and saturated NaHCO3 solution
  2. dry with materialthe organic phase was dried over MgSO4
  3. filtrationthe whole was filtered with suction through a glass frit
  4. additionfilled with 1 cm of silica gel
  5. washthe filter product was washed with heptane/ethyl acetate 1:2
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f92bbfc111ff489abc0e2e6301885b2e
Source dataset
uspto-grants-2012_05
Patent number
US08188002B2

Reaction notes

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