Dimethylformamide → HCID 178439082, compound

HRID 1472232Notes

Reaction equation

HRID 1472232 reaction equation
CN(C)C=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]2[S:15][C:16](=[C:22]([CH3:24])[CH3:23])[CH2:17][CH2:18][C:19]=2[CH:20]=O)=[CH:9][CH:8]=1.C(N(CC)CC)C.CS([Cl:36])(=O)=O>O>[Cl:36]/[CH:20]=[C:19]1/[C:14](=[N:13]/[C:10]2[CH:11]=[CH:12][C:7]([Cl:6])=[CH:8][CH:9]=2)/[S:15][C:16](=[C:22]([CH3:24])[CH3:23])[CH2:17][CH2:18]/1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86670261HCID 86670261, compound

Product 1

HCID 178439082HCID 178439082, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an N,N-dimethylformamide (10 ml) solution of 2-(4-chloro-phenylamino)-6-isopropylidene-5,6-dihydro-4H-thiopyran-3-carbaldehyde (0.44 g), triethylamine (0.23 g) and methanesulfonyl chloride (0.24 g) were added at 0° C. After raising the temperature to room temperature and further stirring for 1 hour, water was added 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]-6-isopropylidene-tetrahydro-thiopyran-(2Z)-ylidene}-(4-chloro-phenyl)-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-ff127324594e409abeb3116d6beb50cc
Source dataset
uspto-grants-2015_04
Patent number
US09012493B2

Reaction notes

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