Reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6](=[N:18][NH2:19])[C:7]2[CH:12]=[CH:11][C:10]([CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.ClS([N:26]=[C:27]=[O:28])(=O)=O.C(OCC)(=O)C.O>CCCCCC>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([C:6](=[N:18][NH:19][C:27]([NH2:26])=[O:28])[C:7]2[CH:8]=[CH:9][C:10]([CH2:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1Participants
6
Procedure
4-chloro-4'-methylsulfonylmethylbenzophenone-hydrazone (1.3 g) and chlorosulfonyl isocyanate (0.63 g) were added to ethyl acetate (100 ml), and the mixture was stirred for one hour at room temperature. Then, water (100 ml) was added, and the mixture was further stirred for 16 hours at room temperature. The reaction mixture was subjected to liquid separation, and the ethyl acetate layer was washed with water and then dried over anhydrous magnesium sulfate. Ethyl acetate was distilled off under reduced pressure. The residual solid was washed with a solvent mixture of ethyl acetate:n-hexane=4:1, to obtain the desired product (1.2 g, melting point: 189° to 191° C., yield: 80%).
Workup
- stirringthe mixture was further stirred for 16 hours at room temperature
- customThe reaction mixture was subjected to liquid separation
- washthe ethyl acetate layer was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- distillationEthyl acetate was distilled off under reduced pressure
- washThe residual solid was washed with a solvent mixture of ethyl acetate
Sources & evidence
- ORD record
- ord-71fa5a93fb9c483491defb7a5b1de773
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05728699
Linked notes
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