Water → HCID 18427783, compound

HRID 1279291Notes

Reaction equation

HRID 1279291 reaction equation
[CH3:1][S:2][C:3](SC)=[C:4]([S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)(=[O:9])=[O:8])[C:5]#[N:6].[Cl:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[C:25]([Cl:33])[C:24]=1[NH:34][NH2:35].O>C(O)C>[NH2:6][C:5]1[N:34]([C:24]2[C:23]([Cl:22])=[CH:28][C:27]([C:29]([F:30])([F:32])[F:31])=[CH:26][C:25]=2[Cl:33])[N:35]=[C:3]([S:2][CH3:1])[C:4]=1[S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[CH:11]=1)(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 962WaterHCID 688223[2,6-Dichloro-4-(trifluoromethyl)phenyl]hydrazineHCID 18427784HCID 18427784, compound

Product 1

HCID 18427783HCID 18427783, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 0.50 g (1.42 mmol) of 3,3-bis-methylthio-2-(3-trifluoromethylphenylsulfonyl)acrylonitrile and 0.35 g (1.42 mmol) of 2,6-dichloro-4-trifluoromethylphenylhydrazine in 10 mL of ethanol was heated at reflux for 2.5 hours, solution occurring as the reaction mixture was warmed. The mixture was stirred overnight at room temperature and was then poured into cold water. The product was extracted into ethyl acetate and the extracts were dried with magnesium sulfate and evaporated. The residues were crystallized from ether, and the product was filtered off and air dried to give 314 mg (40%) of the desired product, m.p. 201-203° C. Anal. Calcd. for C18H11O2N3S2Cl2F6: C, 39.28; H, 2.02; N, 7.64. Found: C, 39.35; H, 2.19; N, 7.48.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperaturewas warmed
  4. extractionThe product was extracted into ethyl acetate
  5. dry with materialthe extracts were dried with magnesium sulfate
  6. customevaporated
  7. customThe residues were crystallized from ether
  8. filtrationthe product was filtered off
  9. customair dried

Sources & evidence

ORD record
ord-7316810a899247f2bd0c360a6af7e2ca
Source dataset
uspto-grants-2002_09
Patent number
US06448265B1

Reaction notes

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