Stannous chloride dihydrate → HCID 15907986, compound

HRID 649872Notes

Reaction equation

HRID 649872 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-686f179c022d4a37b1d67ccf5b8d7934
Source dataset
uspto-grants-2001_08
Patent number
US06271236B1

Reaction notes

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