3,5-Diiodosalicylic acid → HCID 13608340, 화합물

HRID 280036

반응식

HRID 280036 반응식
[I:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[C:4]([C:5]([OH:7])=O)[C:3]=1[OH:12].[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH2:21])=[CH:16][CH:15]=1.P(Cl)(Cl)Cl>ClC1C=CC=CC=1.C(Cl)Cl>[C:22]1([C:20]([C:17]2[CH:16]=[CH:15][C:14]([NH:13][C:5](=[O:7])[C:4]3[CH:8]=[C:9]([I:11])[CH:10]=[C:2]([I:1])[C:3]=3[OH:12])=[CH:19][CH:18]=2)=[CH2:21])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

6

반응물 3

HCID 86313,5-Diiodosalicylic acidHCID 24387Phosphorus trichlorideHCID 20040308HCID 20040308, 화합물

생성물 1

HCID 13608340HCID 13608340, 화합물수율 43.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 7964Chlorobenzene용매

실험 절차

To a refluxing solution of 7.9 g (0.02 mole) of 3,5-diiodosalicylic acid and 4.6 g (0.02 mole) of 1-(4-aminophenyl)-1-phenylethylene in 125 ml of chlorobenzene was added 3 g (0.022 mole) of phosphorus trichloride over a 1 hour period. The resulting mixture was refluxed for 2 hours, cooled, diluted with 100 ml of methylene chloride. The organic phase was washed with 250 ml of water and dried. The extract was evaporated to dryness. After redissolving the residue in minimum amount of methylene chloride, the solution was flash-chromatographed on a silica gel column. The desired component was eluted with 2 liters of methylene chloride/n-hexane. Evaporation of its solvent gave 4.9 g of N-[4-(1-phenylethenyl)phenyl] -2-hydroxy-3,5-diiodobenzamide. Recrystallization from aqueous ethanol gave 4.2 g of purified product, m.p. 173°-174°.

후처리

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. temperaturecooled
  3. washThe organic phase was washed with 250 ml of water
  4. customdried
  5. customThe extract was evaporated to dryness
  6. dissolutionAfter redissolving the residue in minimum amount of methylene chloride
  7. customthe solution was flash-chromatographed on a silica gel column
  8. washThe desired component was eluted with 2 liters of methylene chloride/n-hexane
  9. customEvaporation of its solvent

출처 및 근거

ORD 기록
ord-9d600bc75a5743b39d2325168a77c40e
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04587361

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