Stannous chloride dihydrate → HCID 15907986, compound

HRID 1531205Notes

Reaction equation

HRID 1531205 reaction equation
O.O.[Sn](Cl)Cl.[N:6]([CH:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[S:34])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[O:28])=[CH:22][CH:21]=2)=[CH:13][C:12]=1[Cl:35])[CH3:10])=[N+]=[N-]>CO.C(OCC)(=O)C>[NH2:6][CH:9]([C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[S:34])[NH:19][C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:27]([C:29]3[O:30][CH:31]=[CH:32][CH:33]=3)=[O:28])=[CH:24][CH:25]=2)=[CH:13][C:12]=1[Cl:35])[CH3:10]

Participants

5

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 22612954HCID 22612954, compound

Product 1

HCID 15907986HCID 15907986, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tin(II) chloride dihydrate (0.25 g) in methanol (2.5 mL) is added furan-2-carboxylic acid (4-{3-[4-(1-azido-ethyl)-3-chloro-phenyl]-thioureido}-phenyl)-amide (0.22 g) and the solution is stirred for approximately 15 hours at room temperature. The solution is then diluted with ethyl acetate, washed successively with saturated aqueous sodium bicarbonate then saturated aqueous sodium chloride, then dried over anhydrous sodium sulfate. After removal of the solvent by evaporation under reduced pressure the residue is chromatographed over silica gel (8% methanol in dichloromethane containing 1% triethylamine is used as the eluant) to provide the desired product as a yellow solid.

Workup

  1. washwashed successively with saturated aqueous sodium bicarbonate
  2. dry with materialsaturated aqueous sodium chloride, then dried over anhydrous sodium sulfate
  3. customAfter removal of the solvent
  4. customby evaporation under reduced pressure the residue
  5. customis chromatographed over silica gel (8% methanol in dichloromethane containing 1% triethylamine

Sources & evidence

ORD record
ord-c4b32ab17e174781a28cc5d11ee1cdb4
Source dataset
uspto-grants-2001_03
Patent number
US06197803B1

Reaction notes

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