Acetyl chloride → HCID 18670109, compound

HRID 1059414Notes

Reaction equation

HRID 1059414 reaction equation
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][CH2:15][N:16]1[C:21]2[CH:22]=[C:23]([C:26]([CH3:28])=[O:27])[CH:24]=[CH:25][C:20]=2[S:19][C:18]2[N:29]=[CH:30][CH:31]=[N:32][C:17]1=2.[C:33](Cl)(=[O:35])[CH3:34]>O1CCCC1.CCCCCC.C(OCC)(=O)C.O>[CH3:13][O:14][CH2:15][N:16]1[C:21]2[CH:22]=[C:23]([C:26](=[O:27])[CH2:28][C:33](=[O:35])[CH3:34])[CH:24]=[CH:25][C:20]=2[S:19][C:18]2[N:29]=[CH:30][CH:31]=[N:32][C:17]1=2

Participants

9

Reactant 4

HCID 6367Acetyl chlorideHCID 7912DiisopropylamineHCID 18670297(10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)methyl ketoneHCID 178418339Butyllithium

Product 1

HCID 18670109HCID 18670109, compoundYield 18.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Into 20 ml of ice-cooled solution of 1.27 ml of diisopropylamine in dry tetrahydrofuran was dropped in a nitrogen atmosphere 5.5 ml of a 1.6 M solution of n-butyllithium in hexane. After stirring for 10 minutes, the reaction mixture was cooled to −78° C. Next, 5 ml of a solution of 2.0 g of (10-methoxymethyl-10H-pyrazino[2,3-b][1,4]benzothiazin-8-yl)methyl ketone in dry tetrahydrofuran was added thereto and the mixture was stirred for 30 minutes. After further dropping 700 mg of acetyl chloride thereinto, the reaction mixture was brought back to room temperature. Then the reaction mixture was distributed into water and ethyl acetate and the organic layer was extracted, washed with water, dried over anhydrous sodium sulfate and filtered. The filtrate was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluted with toluene/acetone) to thereby give 420 mg of the title compound as a yellow oily substance.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customwas brought back to room temperature
  3. extractionthe organic layer was extracted
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationThe filtrate was distilled off under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (eluted with toluene/acetone)

Sources & evidence

ORD record
ord-d3a753d7cb0744f8bce44510df7dad7a
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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