Propane sultone → HCID 88491333, compound

HRID 652405Notes

Reaction equation

HRID 652405 reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH2:11]1[CH2:17][S:14](=[O:16])(=[O:15])[O:13][CH2:12]1>C(#N)C>[S:14]([CH2:17][CH2:11][CH2:12][N:1]1[C:10]2[CH:5]([CH2:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)([OH:16])(=[O:15])=[O:13]

Participants

4

Reactant 2

HCID 14264Propane sultoneHCID 694601,2,3,4-Tetrahydroquinoline

Product 1

HCID 88491333HCID 88491333, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a round bottom flask fitted with a stirrer and reflux condenser were placed 50.0 g of tetrahydroquinoline, 48.8 g of 1,3-propanesultone and 500 ml of reagent grade acetonitrile solvent. The mixture was heated at reflux under a nitrogen blanket overnight. The reaction mixture was cooled to ice-bath temperature and the resulting white solid precipitate filtered and washed with cold acetonitrile. A yield of 58 g (60%) of crude product was obtained with a melting point over 200° . Nuclear magnetic resonance (NMR) and mass spectrometry analyses showed the product to be consistent with the assigned structure.

Workup

  1. customIn a round bottom flask fitted with a stirrer
  2. temperaturereflux condenser
  3. temperatureThe mixture was heated
  4. temperatureat reflux under a nitrogen blanket overnight
  5. temperatureThe reaction mixture was cooled to ice-bath temperature
  6. filtrationthe resulting white solid precipitate filtered
  7. washwashed with cold acetonitrile

Sources & evidence

ORD record
ord-e630b06c2de04006a4a2a10905b6e5c1
Source dataset
uspto-grants-1987_06
Patent number
US04672029

Reaction notes

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