2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 8-Methoxypsoralen

HRID 65844노트

반응식

HRID 65844 반응식
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][C:7]=2[CH:6]=[C:5]2[CH:12]=[CH:13][C:14]([O:16][C:4]=12)=[O:15].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:16][C:14]([CH:13]=[CH:12][C:5]=2[CH:6]=[C:7]2[CH:11]=[CH:10][O:9][C:8]=12)=[O:15]

참가 물질

6

반응물 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 774094',5'-Dihydro-8-methoxypsoralen

생성물 1

HCID 41148-Methoxypsoralen수율 70%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A reaction mixture of 218 g of 2,3-dihydroxanthotoxin of Part E, 281 g of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, and 3 liters of toluene was stirred and heated at reflux for 20 hours. The mixture was cooled and poured into 10 liters of 10 percent sodium hydroxide solution containing 5 percent sodium dithionite. The solution was then extracted twice with about 2 liters of chloroform. The combined chloroform extracts were washed with water and dried over sodium sulphate and concentrated to dryness. There was obtained 150 g (70 percent yield), of crude 8-methoxypsoralen which on crystallization from benzene was obtained as white crystals melting at 138°-140° C.

후처리

  1. temperatureheated
  2. temperatureat reflux for 20 hours
  3. temperatureThe mixture was cooled
  4. extractionThe solution was then extracted twice with about 2 liters of chloroform
  5. washThe combined chloroform extracts were washed with water
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated to dryness
  8. customThere was obtained 150 g (70 percent yield)
  9. customof crude 8-methoxypsoralen which on crystallization from benzene

출처 및 근거

ORD 기록
ord-91c551722e7d4cc28c5ab005dc169f27
출처 데이터셋
uspto-grants-1978_12
특허 번호
US04129576

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