Acetyl chloride → HCID 19801652, compound

HRID 1174573Notes

Reaction equation

HRID 1174573 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 boiled under reflux for three hours. The reaction solution was cooled, and triethylamine (60.5 ml) and acetyl chloride (25.9 ml) were added. 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 made basic 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) was obtained in this way; MS (ESI): 293 (M+H+).

Workup

  1. temperatureunder reflux for three hours
  2. temperatureThe reaction solution was cooled
  3. concentrationthe reaction mixture was concentrated
  4. customthe residue was partitioned between hydrochloric acid (6 N) and ethyl acetate
  5. extractionextracted 4 times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe product with the molecular weight of 292.43 (C20H24N2) was obtained in this way

Sources & evidence

ORD record
ord-a1f585e9a8274bfdbdb1c6da76c030ba
Source dataset
uspto-grants-2010_11
Patent number
US07838528B2

Reaction notes

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