2-(4-Bromo-2-dimethylcarbamoylsulfanyl-benzoyl)-malonic acid dimethyl ester → HCID 178498916, compound

HRID 1423911Notes

Reaction equation

HRID 1423911 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:9](=[O:23])[C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][C:11]=1[S:17][C:18](=[O:22])N(C)C)C(OC)=O>C[O-].[Na+].CO>[CH3:1][O:2][C:3]([C:4]1[C:18](=[O:22])[S:17][C:11]2[C:10]([C:9]=1[OH:23])=[CH:15][CH:14]=[C:13]([Br:16])[CH:12]=2)=[O:24]

Participants

3

Reactant 1

HCID 866601322-(4-Bromo-2-dimethylcarbamoylsulfanyl-benzoyl)-malonic acid dimethyl ester

Product 1

HCID 178498916HCID 178498916, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 2-(4-bromo-2-dimethylcarbamoylsulfanyl-benzoyl)-malonic acid dimethyl ester (11.2 g, 26.79 mmol) in 0.5 M NaOMe/MeOH solution (214 mL) was heated to reflux for 6 h. After cooling overnight, the precipitated solid was collected by filtration and rinsed with MeOH followed by ether. The solid was dried in vacuo to provide 7-bromo-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (5.37 g) as a sodium salt. 1H NMR (200 MHz, DMSO-d6): δ (ppm)=7.98 (d, J=8.5 Hz, 1H), 7.50 (d, J=1.9 Hz, 1H), 7.38 (dd, J=8.5, 1.8 Hz, 1H), 3.56 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 6 h
  3. temperatureAfter cooling overnight
  4. filtrationthe precipitated solid was collected by filtration
  5. washrinsed with MeOH
  6. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-d97709de15af40e29139565eddbf8b1d
Source dataset
uspto-grants-2015_01
Patent number
US08927591B2

Reaction notes

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