Dichloromethane → HCID 86658453, compound

HRID 1515376Notes

Reaction equation

HRID 1515376 reaction equation
[CH3:1]S(Cl)(=O)=O.C(Cl)Cl.O[CH2:10][CH2:11]/[C:12](=[CH:22]\[S:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)/[C:13](=[S:21])[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>O>[C:24]1([S:23]/[CH:22]=[C:12]2/[C:13](=[N:14]/[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)/[S:21][CH2:10][CH2:11]/2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:15]1([N:14]2[CH2:10][CH2:11][C:12](=[C:22]([S:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH3:1])[C:13]2=[S:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86658451HCID 86658451, compound

Product 2

HCID 86658453HCID 86658453, compoundHCID 178503135HCID 178503135, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.13 g of methanesulfonyl chloride was added to 10 ml of methylene chloride suspension including 0.4 g of (E)-4-hydroxy-N-phenyl-2-(phenylthiomethylene)butanethioamide and 0.11 g of triethylamine. The resulting solution was stirred at room temperature for 2 hours, and added with water, extracted with ethyl acetate. The organic layer was washed with brine, and dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.05 g of (Z)—N-((E)-3-(phenylthiomethylene)dihydrothiophen-2(3H)-ylidene) aniline and 0.05 g of 1-phenyl-3-(1-(phenylthio)ethylidene)pyrrolidine-2-thione.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e43f3a318db04d8280c33a8f0e125e03
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

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