1,3-Cyclohexanedione → 3-Oxo-1-cyclohexenyl 2,4-dibromo-3-(aminocarbonylmethoxy)benzoate

HRID 1835865Notes

Reaction equation

HRID 1835865 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH2:12][C:13]([NH2:15])=[O:14])=[C:9]([Br:16])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:17]1(=O)[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH2:18]1>CN(C1C=CN=CC=1)C.C(Cl)Cl.Cl>[Br:1][C:2]1[C:10]([O:11][CH2:12][C:13]([NH2:15])=[O:14])=[C:9]([Br:16])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][C:17]1[CH2:22][CH2:21][CH2:20][C:19](=[O:23])[CH:18]=1)=[O:5]

Participants

6

Reactant 2

HCID 104341,3-CyclohexanedioneHCID 120568552,4-Dibromo-3-(aminocarbonylmethoxy)benzoic acid

Product 1

HCID 120568563-Oxo-1-cyclohexenyl 2,4-dibromo-3-(aminocarbonylmethoxy)benzoate

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.400 g (1.10 mmol) of 2,4-dibromo-3-(aminocarbonylmethoxy)benzoic acid, 0.140 g (1.20 mmol) of cyclohexane-1,3-dione, 0.222 g (1.10 mmol) of N′-(3-dimethyl-aminopropyl) -N-ethylcarbodiimide hydrochloride and 0.001 g of DMAP was stirred for 14 hours at RT in 15 ml of CH2Cl2. The mixture was subsequently diluted with CH2Cl2 and with 0.5 N HCl, and washed with water, with saturated NaHCO3 solution and again with water. After the combined organic phases have been dried over Na2SO4 and concentrated completely, 3-oxo-1-cyclohexenyl 2,4-dibromo-3-(aminocarbonylmethoxy)benzoate was obtained as a yellow resin, which had sufficient purity for the subsequent reaction.

Workup

  1. washwashed with water, with saturated NaHCO3 solution and again with water
  2. dry with materialAfter the combined organic phases have been dried over Na2SO4
  3. concentrationconcentrated completely

Sources & evidence

ORD record
ord-0d6ee57029b84466a9322d21cbbe2ab1
Source dataset
uspto-grants-2004_08
Patent number
US06774086B2

Reaction notes

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