Potassium cyanate → 4-Cyano-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

HRID 127509노트

반응식

HRID 127509 반응식
[CH2:1]([S:4][C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:2]#[CH:3].[O-][C:15]#[N:16].[K+]>C(O)C.C(N(CC)CC)C.O>[C:15]([CH:3]1[C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][C:5]=2[S:4][CH2:1][CH2:2]1)#[N:16]

참가 물질

6

반응물 2

HCID 11378442Potassium cyanateHCID 202847712-[(Prop-2-yn-1-yl)sulfanyl]-1H-indole

생성물 1

HCID 147356314-Cyano-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole수율 69%

시약·촉매·용매 3

HCID 702Ethanol용매2회HCID 962Water용매HCID 8471Triethylamine용매

실험 절차

The product of the above (2) (13.2 g) is dissolved in a mixture of ethanol (300 ml) and triethylamine (20 ml). The solution is refluxed for 1 hour and further 2 hours after addition of a solution of potassium cyanate (25 g) in a mixture of ethanol (170 ml) and water (80 ml) and evaporated to remove the solvent. The residue is extracted with ether after addition of water. The extract is washed with water, dried and evaporated to remove the solvent. The oily residue (15 g) is chromatographed on an column of silica gel (450 g) and eluted with benzene. The eluate is condensed to give the title compound as crystals melting at 125°-126° C. Yield: 69%

후처리

  1. temperatureThe solution is refluxed for 1 hour and further 2 hours
  2. customevaporated
  3. customto remove the solvent
  4. extractionThe residue is extracted with ether
  5. additionafter addition of water
  6. washThe extract is washed with water
  7. customdried
  8. customevaporated
  9. customto remove the solvent
  10. customThe oily residue (15 g) is chromatographed on an column of silica gel (450 g)
  11. washeluted with benzene
  12. customcondensed

출처 및 근거

ORD 기록
ord-4667abd387504f358b99fae953c62ba0
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04256640

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