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

HRID 1034324
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HRID 1034324 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b34ba0936ec743b8aba301b1a89049fe
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05314918

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