Sodium Thiosulfate → HCID 23681402, compound

HRID 224234Notes

Reaction equation

HRID 224234 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][NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])=[N:19][N:18]=[C:17]1[CH2:33]Cl.[S:36]([O-:40])([O-:39])(=[O:38])=[S:37].[Na+:41].[Na+]>C(O)C.O>[Na+:41].[S:36]([OH:40])([O-:39])(=[O:38])=[S:37].[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:17]([CH2:33][SH:36])=[N:18][N:19]=[C:20]1[CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]

Participants

5

Reactant 2

HCID 24477Sodium ThiosulfateHCID 15573091HCID 15573091, compound

Product 1

HCID 23681402HCID 23681402, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2',5-dichloro-2-(5-carbobenzoxyaminomethyl-3-chloromethyl-1,2,4-triazol-4-yl)benzophenone (12.8 g) in ethanol (600 ml) is added a solution of sodium thiosulfate (7.2 g) in water (200 ml), and the resultant mixture is refluxed for 1.5 hours. The reaction mixture is evaporated under reduced pressure to remove the solvent, whereby 2',5-dichloro-2-(3-carbobenzoxyaminomethyl-5-mercaptomethyl-1,2,4-triazol-4-yl)benzophenone thiosulfate monosodium salt is obtained. This substance is dissolved in water (600 ml), mixed with thiol type thiamine sodium salt (10.8 g) and stirred overnight. The colorless precipitate is filtered, washed with water and dissolved in a mixture of chloroform and methanol. The organic layer is dried over sodium sulfate and the solvent is evaporated under reduced pressure. The residue is chromatographed on a column of silica gel, which is eluted with ethyl acetate to give bis[4-{2-(2-chlorobenzoyl)-4-chlorophenyl}-5-carbobenzoxyaminomethyl-1,2,4-triazol-3-methyl]disulfide (7.4 g) as crystals melting at 113°-115° C. This compound is recrystallized from ethyl acetate/n-hexane to give colorless crystals.

Workup

  1. customThe reaction mixture is evaporated under reduced pressure
  2. customto remove the solvent

Sources & evidence

ORD record
ord-d4e44f3f62914de4b040e1b7d3a3d850
Source dataset
uspto-grants-1980_11
Patent number
US04231930

Reaction notes

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