Carbon Disulfide → (3,4,4-trifluoro-3-butenyl) N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yl)dithiocarbamate

HRID 1253232노트

반응식

HRID 1253232 반응식
[OH-].[Na+].[NH2:3][C:4]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.[C:15](=[S:17])=[S:16].Br[CH2:19][CH2:20][C:21]([F:25])=[C:22]([F:24])[F:23]>CS(C)=O.O>[CH3:13][C:10]1([CH3:14])[CH2:9][C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([NH:3][C:15](=[S:17])[S:16][CH2:19][CH2:20][C:21]([F:25])=[C:22]([F:24])[F:23])[C:12]=2[O:11]1

참가 물질

7

반응물 4

HCID 6348Carbon DisulfideHCID 14798Sodium HydroxideHCID 663334-Bromo-1,1,2-trifluorobut-1-eneHCID 916972,2-Dimethyl-2,3-dihydro-1-benzofuran-7-amine

생성물 1

HCID 53946512(3,4,4-trifluoro-3-butenyl) N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yl)dithiocarbamate

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

Sodium hydroxide (3.7 ml, 20M) was added to a stirred solution of 7-amino-2,3-dihydro-2,2-dimethylbenzofuran (10 grams, 0.061 mole) in dimethyl sulfoxide (31 ml). Upon completion of addition, carbon disulfide (6.06 grams, 0.08 mole) was added. The reaction mixture was stirred for one hour at ambient temperature, then cooled to 0° C. at which time 4-bromo-1,1,2-trifluoro-1-butene was added dropwise. The reaction mixture was stirred at ambient temperature overnight. The reaction mixture was diluted with water (400 ml) and extracted with diethyl ether. The extract was dried (sodium sulfate) and concentrated under reduced pressure leaving a residue. This residue was passed through a column of silica gel, eluting with hexane:diethyl ether (9:1). Appropriate fractions were combined and concentrated under reduced pressure, yielding (3,4,4-trifluoro-3-butenyl) N-(2,3-dihydro-2,2-dimethylbenzofuran-7-yl)dithiocarbamate (Compound A12). The NMR spectrum was consistent with the proposed structure.

후처리

  1. additionwas added
  2. additionwas added dropwise
  3. stirringThe reaction mixture was stirred at ambient temperature overnight
  4. extractionextracted with diethyl ether
  5. dry with materialThe extract was dried (sodium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customleaving a residue
  8. washeluting with hexane:diethyl ether (9:1)
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1a660b4b04bf4134843eb28e79896b52
출처 데이터셋
uspto-grants-1988_05
특허 번호
US04748186

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