Acetyl chloride → 3-Dimethylaminomethyl-tetrahydrothiopyran-4-one hydrochloride

HRID 131534Notes

Reaction equation

HRID 131534 reaction equation
[S:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.[Cl-].[CH3:9][N+:10](=[CH2:12])[CH3:11].C([Cl:16])(=O)C>C(#N)C>[ClH:16].[CH3:9][N:10]([CH2:12][CH:3]1[C:4](=[O:7])[CH2:5][CH2:6][S:1][CH2:2]1)[CH3:11]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 66173Tetrahydrothiopyran-4-oneHCID 11051579Dimethylmethylenammonium chloride

Product 1

HCID 133173673-Dimethylaminomethyl-tetrahydrothiopyran-4-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

5.00 g tetrahydrothiopyran-4-one were dissolved in 15 ml acetonitrile, and 4.03 g N,N-dimethyl-methylenammonium chloride, followed by 40 μl acetyl chloride, were added. After the mixture had been stirred at a bath temperature of 60° C. for 45 minutes, it was stirred at room temperature for 60 hours and the precipitate formed was filtered off with suction and dried. 8.17 g 3-dimethylaminomethyl-tetrahydrothiopyran-4-one hydrochloride with a melting point of 155-157° C. were obtained. The corresponding base was liberated from this with methylene chloride and sodium hydroxide solution (32 percent strength by weight).

Workup

  1. additionwere added
  2. stirringit was stirred at room temperature for 60 hours
  3. customthe precipitate formed
  4. filtrationwas filtered off with suction
  5. customdried

Sources & evidence

ORD record
ord-70049f94f63242df8c49a82ecf34f854
Source dataset
uspto-grants-2008_06
Patent number
US07384961B2

Reaction notes

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