Iodine → HCID 178443173, compound

HRID 1076274Notes

Reaction equation

HRID 1076274 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]=[C:12]([NH:16][C:17]2[CH:22]=[C:21]([NH:23][C:24](=[O:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:20]=[CH:19][C:18]=2[Cl:39])[NH:11]1.II.[N:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:10]1[C:14](=[O:15])[C-:13]([N+:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:12]([NH:16][C:17]2[CH:22]=[C:21]([NH:23][C:24](=[O:38])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH:20]=[CH:19][C:18]=2[Cl:39])=[N:11]1

Participants

4

Reactant 3

HCID 807IodineHCID 1049PyridineHCID 13907351HCID 13907351, compound

Product 1

HCID 178443173HCID 178443173, compound

Procedure

A mixture of 7.1 g of 1-(2,4,6-trichlorophenyl)-3-[2-chloro-5-(n-tetradecanamido)anilino]-5-pyrazolone, 2.5 g of iodine and 100 ml of pyridine was heated on a steam bath for 5 hours. After cooling, the reaction mixture was poured into a large volume of ice water. The precipitate was collected by filtration and dried. The powder was recrystallized from a solvent mixture of hexane and ethyl acetate to give 4.8 g of Compound 18 as yellow crystals having a melting point of 124° to 128°C.

Workup

  1. temperaturewas heated on a steam bath for 5 hours
  2. temperatureAfter cooling
  3. filtrationThe precipitate was collected by filtration
  4. customdried
  5. customThe powder was recrystallized from a solvent mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-206809a17a854802bae5301904f4d9cc
Source dataset
uspto-grants-1976_05
Patent number
US03956339

Reaction notes

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