Benzene → 5-chloro-2-(3-carbobenzoxyaminomethyl-5-iodomethyl-4H-1,2,4-triazol-4-yl)-benzophenone

HRID 25951Notes

Reaction equation

HRID 25951 reaction equation
[I-:1].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:18]2[C:22]([CH2:23]Cl)=[N:21][N:20]=[C:19]2[CH2:25][NH:26][C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])=[C:8]([CH:17]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10].O.C1C=CC=CC=1>C(#N)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:18]2[C:22]([CH2:23][I:1])=[N:21][N:20]=[C:19]2[CH2:25][NH:26][C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])=[C:8]([CH:17]=1)[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:10]

Participants

6

Reactant 4

HCID 241BenzeneHCID 962WaterHCID 5238Sodium IodideHCID 213257095-chloro-2-(3-carbobenzoxyaminomethyl-5-chloromethyl-4H-1,2,4-triazol-4-yl)-benzophenone

Product 1

HCID 213256885-chloro-2-(3-carbobenzoxyaminomethyl-5-iodomethyl-4H-1,2,4-triazol-4-yl)-benzophenoneYield 61.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of sodium iodide (1.51 g) in acetonitrile (30 ml), 5-chloro-2-(3-carbobenzoxyaminomethyl-5-chloromethyl-4H-1,2,4-triazol-4-yl)-benzophenone (5.0 g) is added, and the resultant mixture is stirred at room temperature for 18 hours. The reaction mixture is poured into water (100 ml) and shaken with benzene (50 ml) twice. The benzene layer is washed with water (100 ml) twice, dried over magnesium sulfate and evaporated under reduced pressure to remove the benzene. The residue is chromatographed on a column of silica gel, which is eluted with ethyl acetate to give 5-chloro-2-(3-carbobenzoxyaminomethyl-5-iodomethyl-4H-1,2,4-triazol-4-yl)-benzophenone (3.61 g). The product is recrystallized from methylene chloride/ether to give crystals melting at 133° to 134° C. (decomp.).

Workup

  1. washThe benzene layer is washed with water (100 ml) twice
  2. dry with materialdried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customto remove the benzene
  5. customThe residue is chromatographed on a column of silica gel, which
  6. washis eluted with ethyl acetate

Sources & evidence

ORD record
ord-61d59572056546db84c48f4d24f2e9a4
Source dataset
uspto-grants-1979_04
Patent number
US04147700

Reaction notes

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