1-Butanol → (2-Butoxy-2-oxoethyl)azanium chloride

HRID 1817326Notes

Reaction equation

HRID 1817326 reaction equation
Cl.[NH2:2][CH2:3][C:4]([OH:6])=[O:5].S(Cl)([Cl:9])=O.[CH2:11](O)[CH2:12][CH2:13][CH3:14]>>[Cl-:9].[CH2:11]([O:5][C:4](=[O:6])[CH2:3][NH3+:2])[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 22316Glycine HydrochlorideHCID 24386Thionyl Chloride

Product 1

HCID 133112781(2-Butoxy-2-oxoethyl)azanium chloride

Conditions

Temperature
70 °C

Procedure

Glycine hydrochloride (400 g, 3.58 mol) was suspended in 8 L of n-butanol and thionyl chloride (1.37 L, 18.84 mol) was added slowly dropwise (exotherm). After addition was complete, the reaction was heated to 70° C. overnight. The reaction could be followed by spotting directly on TLC, pumping off the volatiles, eluting with 10% MeOH/CHCl3 saturated with NH3, and staining in ninhydrin. The next day the reaction was stripped to dryness under vacuum and the residue was triturated with heptane/EtOAc to give the product as a white solid after drying on a filter under Nitrogen.

Workup

  1. additionAfter addition
  2. customThe reaction
  3. washeluting with 10% MeOH/CHCl3 saturated with NH3
  4. customthe residue was triturated with heptane/EtOAc

Sources & evidence

ORD record
ord-7f8ccf60aff74019a55c353a09b34407
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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