Dimethylformamide → HCID 178435100, compound

HRID 1472237Notes

Reaction equation

HRID 1472237 reaction equation
CN(C)C=O.[CH3:6][C:7]1([CH3:24])[C:12](=[CH2:13])[S:11][C:10]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[C:9]([CH:22]=O)[CH2:8]1.C(N(CC)CC)C.CS([Cl:36])(=O)=O>O>[Cl:36]/[CH:22]=[C:9]1/[C:10](=[N:14]/[C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)/[S:11][C:12](=[CH2:13])[C:7]([CH3:24])([CH3:6])[CH2:8]/1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86670263HCID 86670263, compound

Product 1

HCID 178435100HCID 178435100, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an N,N-dimethylformamide (5 ml) solution of 5,5-dimethyl-6-methylene-2-p-tolylamino-5,6-dihydro-4H-thiopyran-3-carbaldehyde (0.26 g), triethylamine (0.14 g) and methanesulfonyl chloride (0.16 g) were added at 0° C. After raising the temperature to room temperature and further stirring for 1 hour, water was added thereto and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to obtain a crude product of {3-[1-chloro-(E)-methylidene]-5,5-dimethyl-6-methylene-tetra hydro-thiopyran-(2Z)-ylidene}-p-tolyl-amine.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated saline solution, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9ad647a5fca34305b0e3aaaadb0f0ed6
Source dataset
uspto-grants-2015_04
Patent number
US09012493B2

Reaction notes

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