Triethylamine → HCID 22323657, compound

HRID 1954442Notes

Reaction equation

HRID 1954442 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][OH:5].[CH3:6][S:7](Cl)(=[O:9])=[O:8].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CC#N>[CH3:6][S:7]([CH:4]([OH:5])[CH2:3][CH2:2][Cl:1])(=[O:9])=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 123133-Chloro-1-propanolHCID 31297Methanesulfonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 22323657HCID 22323657, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 3-chloro-1-propanol (5.02 mL, 60 mmole) in CH3CN (200 mL) was added methanesulfonyl chloride (10.4 g, 90 mmole) and triethyl amine (13 mL, 90 mmole). The reaction mixture was stirred at room temperature for 12 hours under an argon atmosphere. 200 mL of saturated NaHCO3 (aq) was added and the stirring was continued for 15 minutes. The mixture was extracted several times with ether. The combined ether layers were dried over Na2SO4, the Na2SO4 was filtered and the filtrate was evaporated to give 10 g (96.6%) of the title compound: TLC (Rf: 0.3; 20% EtOAc/Hexane), 1H NMR (CDCl3) δ 2.2 (m, 2 H, CH2), 3.0 (s, 3 H, CH3), 3.6 (t, 2 H, CH2), 4.4 (t, 2 H, CH2). 13C NMR (CDCl3): δ 31.5 (CH2), 37.0 (CH3), 40.2 (CH2), 66.3 (CH2).

Workup

  1. waitthe stirring was continued for 15 minutes
  2. extractionThe mixture was extracted several times with ether
  3. dry with materialThe combined ether layers were dried over Na2SO4
  4. filtrationthe Na2SO4 was filtered
  5. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-14d3c68a57fb488eb8532eab163b5213
Source dataset
uspto-grants-2000_09
Patent number
US06121433

Reaction notes

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