Acetyl chloride → HCID 19801652, compound

HRID 2043092Notes

Reaction equation

HRID 2043092 reaction equation
CS(OC[CH2:7][CH:8](OS(C)(=O)=O)[CH:9](OS(C)(=O)=O)[CH2:10][CH2:11]OS(C)(=O)=O)(=O)=O.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.O1CCO[CH2:37][CH2:36]1.C(Cl)(=O)C.[CH2:45]([N:47]([CH2:50][CH3:51])[CH2:48][CH3:49])[CH3:46]>>[CH2:27]([N:34]1[CH2:37][CH2:36][CH:45]2[N:47]([CH2:50][C:51]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:48][CH2:49][CH:46]12)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 5

HCID 6367Acetyl chlorideHCID 7504BenzylamineHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 86617117HCID 86617117, compound

Product 1

HCID 19801652HCID 19801652, compound

Procedure

A mixture of 1,3,4,6-tetramethanesulfonyloxyhexane (20.6 g), benzylamine (39.6 ml) and dioxane (550 ml) was refluxed for three hours. Triethylamine (60.5 ml) and acetyl chloride (25.9 ml) were added to the cooled reaction solution. After 40 minutes, the reaction mixture was concentrated and the residue was partitioned between hydrochloric acid (6 N) and ethyl acetate. The aqueous phase was basified with sodium hydroxide solution (10 N) and extracted 4 times with ethyl acetate. The combined organic phases were dried over magnesium sulfate and concentrated. The product with the molecular weight of 292.43 (C20H24N2); MS (ESI): 293 (M+H+) was obtained in this way.

Workup

  1. temperaturewas refluxed for three hours
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was partitioned between hydrochloric acid (6 N) and ethyl acetate
  4. extractionextracted 4 times with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated
  7. customMS (ESI): 293 (M+H+) was obtained in this way

Sources & evidence

ORD record
ord-f1d3b08523104ccc897de7bde63ee4ea
Source dataset
uspto-grants-2013_11
Patent number
US08586609B2

Reaction notes

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