Ethyl bromoacetate → HCID 12852681, compound

HRID 1156827Notes

Reaction equation

HRID 1156827 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][C:6](=O)[C:5]([NH:10][C:11](=[O:16])[CH2:12][C:13](=[O:15])[CH3:14])=[CH:4][CH:3]=1.[O-]CC.[Na+].[Na].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>CO>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][N:10]1[C:11](=[O:16])[C:12]([C:13](=[O:15])[CH3:14])=[C:6]2[CH:7]=[CH:8][C:2]([Cl:1])=[CH:3][CH:4]=[C:5]12)[CH3:28]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 20534014HCID 20534014, compound

Product 1

HCID 12852681HCID 12852681, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 1-[(4-chloro-7-oxo-1,3,5-cycloheptatrien-1-yl)amino]-1,3-butanedione (5.8 g) and sodium ethoxide solution, prepared by dissolving 1.1 g of sodium in 200 ml of anhydrous, methanol-free ethanol, was heated at reflux for 5 hr. Thereafter, ethyl bromoacetate (10 ml) was added dropwise to the hot solution and refluxing was continued for an additional 10 min. The reaction mixture was evaporated to dryness. The residue was dissolved in chloroform and the solution filtered through a column of silica gel. Evaporation of the eluate gave 3.75 g of 3-acetyl-6-chloro-1,2-dihydro-2-oxocyclohepta[b]pyrrole-1-acetic acid ethyl ester, identical to the compound obtained from method A. Crystallization of the latter compound gave the product with mp 183.5° C.; nmr (CDCl3) δ1.27 (t, 3H), 2.7 (s, 3H), 4.2 (q, 2H), 4.85 (s, 2H), 6.85-9.3 (m, 4H); ir (white mineral oil) 1725, 1685 cm-1 ; uvλmax (MeOH) 293 nm (ε21,995), 256 (14,630), 231 (16,945); Anal Calcd for C15H14ClNO4 : C, 58.55% H, 4.59% N, 4.55%; Found: C, 58.53% H, 4.60% N, 4.54%.

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for 5 hr
  4. temperaturerefluxing
  5. customThe reaction mixture was evaporated to dryness
  6. dissolutionThe residue was dissolved in chloroform
  7. filtrationthe solution filtered through a column of silica gel
  8. customEvaporation of the

Sources & evidence

ORD record
ord-d299eb4a69f145509391ab00d49ab2a5
Source dataset
uspto-grants-1982_06
Patent number
US04337265

Reaction notes

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