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Water → 4-Chloro-4'-methylsulfonylmethylbenzophenone-semicarbazone

HRID 2094
Notes
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Reaction equation

HRID 2094 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]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70918Chlorosulfonyl isocyanateHCID 867522794-Chloro-4'-methylsulfonylmethylbenzophenone-hydrazone

Product 1

HCID 542023254-Chloro-4'-methylsulfonylmethylbenzophenone-semicarbazoneYield 81.5%

Reagents, catalysts & solvents 1

HCID 8058
Hexane
Solvent

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

  1. stirringthe mixture was further stirred for 16 hours at room temperature
  2. customThe reaction mixture was subjected to liquid separation
  3. washthe ethyl acetate layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationEthyl acetate was distilled off under reduced pressure
  6. washThe residual solid was washed with a solvent mixture of ethyl acetate

Sources & evidence

ORD record
ord-71fa5a93fb9c483491defb7a5b1de773
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05728699

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes