Trimethylamine → HCID 178478210, compound

HRID 1515384Notes

Reaction equation

HRID 1515384 reaction equation
CN(C)C.CN(C=O)C.Cl/[CH:11]=[C:12]1/[C:13](=[N:22]/[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)/[S:14][CH:15]2[CH:20]([CH2:21]/1)[CH2:19][CH2:18][CH:17]=[CH:16]2.[C:30]1([SH:36])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O>[Cl:29][C:26]1[CH:27]=[CH:28][C:23](/[N:22]=[C:13]2\[S:14][CH:15]3[CH:20]([CH2:21]\[C:12]\2=[CH:11]/[S:36][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:19][CH2:18][CH:17]=[CH:16]3)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 1146TrimethylamineHCID 6228Dimethylformamide2×HCID 7969ThiophenolHCID 178478429HCID 178478429, compound

Product 1

HCID 178478210HCID 178478210, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

65 mg of trimethylamine and 1 ml of DMF solution including {3-[1-chloro-(E)-methylidene]-3,4,4a,5,6,8a-hexahydro-thiochromene-(2Z)-ylidene}-(4-chloro-phenyl)-amine were added to 2 ml of DMF solution including 47 mg of thiophenol at 0° C. The resulting solution was stirred at room temperature for an additional 30 minutes, and added with water, and then extracted with ethyl acetate. The organic layer was washed with brine, dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 0.17 g of the title compound.

Workup

  1. customat 0° C
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e583d78e8a5a42c0ab2744bcc0448f4e
Source dataset
uspto-grants-2012_07
Patent number
US08222430B2

Reaction notes

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