Potassium Iodide → 2',5-dichloro-2-(3-carbobenzoxyaminomethyl-5-diethylaminomethyl-4H-1,2,4-triazol-4-yl)-benzophenone

HRID 25950Notes

Reaction equation

HRID 25950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:35])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([CH2:21]Cl)=[N:19][N:18]=[C:17]1[CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26].[I-].[K+].[CH2:38]([NH:40][CH2:41][CH3:42])[CH3:39]>CO.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:35])[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N:16]1[C:20]([CH2:21][N:40]([CH2:41][CH3:42])[CH2:38][CH3:39])=[N:19][N:18]=[C:17]1[CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 8021DiethylamineHCID 15573091HCID 15573091, compound

Product 1

HCID 213256792',5-dichloro-2-(3-carbobenzoxyaminomethyl-5-diethylaminomethyl-4H-1,2,4-triazol-4-yl)-benzophenone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2',5-dichloro-2-(3-carbobenzoxyaminomethyl-5-chloromethyl-4H-1,2,4-triazol-4yl)-benzophenone (1.32 g) in methanol (20 ml) and chloroform (20 ml), potassium iodide (0.4 g) and diethylamine (3 ml) are added, and the resultant mixture is refluxed for 5 hours. The reaction mixture is evaporated under reduced pressure to remove the solvent, and the residue is extracted with ethyl acetate. The ethyl acetate layer is washed with water, dried, and evaporated under reduced pressure to remove the ethyl acetate. The residue is treated with ether to give 2',5-dichloro-2-(3-carbobenzoxyaminomethyl-5-diethylaminomethyl-4H-1,2,4-triazol-4-yl)-benzophenone (1.1 g). The product is recrystallized from ether-ethyl acetate to give crystals melting at 89° to 94° C.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customto remove the solvent
  3. extractionthe residue is extracted with ethyl acetate
  4. washThe ethyl acetate layer is washed with water
  5. customdried
  6. customevaporated under reduced pressure
  7. customto remove the ethyl acetate
  8. additionThe residue is treated with ether

Sources & evidence

ORD record
ord-54b1c86c55a645a287999f437bbacbbe
Source dataset
uspto-grants-1979_04
Patent number
US04147700

Reaction notes

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