Ammonia → 2,2-Dimethyl-6-trifluoromethylthio-2H-1-benzopyran

HRID 1656465노트

반응식

HRID 1656465 반응식
[SH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[CH:8]=[CH:7][C:6]=2[CH:13]=1.N.[F:15][C:16](I)([F:18])[F:17]>C(OCC)(=O)C>[CH3:12][C:9]1([CH3:11])[CH:8]=[CH:7][C:6]2[CH:13]=[C:2]([S:1][C:16]([F:18])([F:17])[F:15])[CH:3]=[CH:4][C:5]=2[O:10]1

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 16843TrifluoroiodomethaneHCID 150360126-mercapto-2,2-dimethyl-2H-1-benzopyran

생성물 1

HCID 147482442,2-Dimethyl-6-trifluoromethylthio-2H-1-benzopyran수율 59.6%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

1.45 g of 6-mercapto-2,2-dimethyl-2H-1-benzopyran (prepared as described in Preparation 6) was suspended in 30 ml of liquid ammonia, and 8.23 g of trifluoromethyl iodide were then added to the suspension at -60° C. in an atmosphere of nitrogen. The resulting mixture was then irradiated at -65° C. for 2 hours and then at 25° C. for 2 hours, using a low pressure mercury lamp. At the end of this time, the reaction mixture was diluted with ethyl acetate and washed with dilute aqueous hydrochloric acid, with water, with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. The organic layer was then dried over anhydrous sodium sulfate and concentrated by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 20:2:1 by volume mixture of cyclohexane, chloroform and ethyl acetate as the eluent, to afford 1.17 g of the title compound as an oil.

후처리

  1. additionwere then added to the suspension at -60° C. in an atmosphere of nitrogen
  2. customThe resulting mixture was then irradiated at -65° C. for 2 hours
  3. washwashed with dilute aqueous hydrochloric acid, with water, with an aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  5. concentrationconcentrated by distillation under reduced pressure
  6. customThe resulting residue was purified by column chromatography through silica gel
  7. additionby volume mixture of cyclohexane, chloroform and ethyl acetate as the eluent

출처 및 근거

ORD 기록
ord-b466f57a47be4a01b90bbd588d9412a7
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05254578

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