3,5-Diiodosalicylic acid → HCID 13608340, compound

HRID 280036

Reaction equation

HRID 280036 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

HCID 13608340HCID 13608340, compoundYield 43.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7964ChlorobenzeneSolvent

Procedure

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°.

Workup

  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

Sources & evidence

ORD record
ord-9d600bc75a5743b39d2325168a77c40e
Source dataset
uspto-grants-1986_05
Patent number
US04587361

Linked notes

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