Dimethylformamide → Ethyl 7-((dimethylamino)thioxomethoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate

HRID 1034324Notes

Reaction equation

HRID 1034324 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=2[C:3]=1[CH2:18][CH2:19][CH3:20].[H-].[Na+].CN(NC(Cl)=[S:28])C.[CH3:30][N:31]([CH3:34])[CH:32]=O>C(Cl)Cl>[CH3:34][N:31]([C:32](=[S:28])[O:1][C:2]1[CH:17]=[CH:16][C:5]2[C:6](=[O:15])[CH:7]=[C:8]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[O:9][C:4]=2[C:3]=1[CH2:18][CH2:19][CH3:20])[CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 4196515Ethyl 7-hydroxy-4-oxo-8-propyl-4H-chromene-2-carboxylateHCID 14673822Dimethylaminothiocarbamylchloride

Product 1

HCID 13744907Ethyl 7-((dimethylamino)thioxomethoxy)-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 7-hydroxy-4-oxo-8-n-propyl-4H-1-benzopyran-2-carboxylate (1 g) in anhydrous dimethylformamide (4 ml) is cooled to 0° and treated under nitrogen with sodium hydride (50% dispersion in mineral oil, 180 mg) with stirring for 30 minutes. Dimethylaminothiocarbamylchloride (465 mg) is added and the mixture is stirred 15 minutes at 0°, warmed to 80° and maintained as such for 18 hours. The mixture is cooled, diluted with methylene chloride (50 ml) and washed with water (3×100 ml)), dried over sodium sulfate and reduced to dryness in vacuo. The residue is recrystallized from ethyl acetate and hexane to yield the title compound.

Workup

  1. stirringthe mixture is stirred 15 minutes at 0°
  2. temperaturewarmed to 80°
  3. temperaturemaintained as such for 18 hours
  4. temperatureThe mixture is cooled
  5. washwashed with water (3×100 ml)),
  6. dry with materialdried over sodium sulfate
  7. customThe residue is recrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-b34ba0936ec743b8aba301b1a89049fe
Source dataset
uspto-grants-1994_05
Patent number
US05314918

Reaction notes

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