HCID 86660136, compound → HCID 178498908, compound

HRID 1746211Notes

Reaction equation

HRID 1746211 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH:4]([C:9](=[O:23])[C:10]1[CH:15]=[C:14]([Br:16])[CH:13]=[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][C:14]([Br:16])=[CH:13][CH:12]=2)=[O:24]

Participants

3

Reactant 1

HCID 86660136HCID 86660136, compound

Product 1

HCID 178498908HCID 178498908, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 23694274Sodium methanolate methanolSolvent

Procedure

A mixture of 2-(5-bromo-2-dimethylcarbamoylsulfanyl-benzoyl)-malonic acid dimethyl ester (4.9 g, 11.71 mmol) in 0.5 M NaOMe/MeOH solution (94 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 6-bromo-4-hydroxy-2-oxo-2H-thiochromene-3-carboxylic acid methyl ester (1.9 g) as a sodium salt. 1H NMR (200 MHz, DMSO-d6): δ (ppm)=8.164 (s, 1H), 7.524 (d, 1H), 7.23 (d, 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-10f671b64c7242a8af94af0aaf373875
Source dataset
uspto-grants-2015_10
Patent number
US09149476B2

Reaction notes

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