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

HRID 17985Notes

Reaction equation

HRID 17985 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

To a suspension of glycine hydrochloride (400 g, 3.58 mol) in n-butanol (8 L), thionyl chloride (1.37 L, 18.84 mol) was added slowly dropwise. After addition was complete, the reaction was heated at 70° C. overnight. The product mixture was concentrated under vacuum and the residue was triturated with a mixture of heptane/ethyl acetate. The white solid precipitated was filtered and dried under a stream of dry nitrogen to provide the title compound.

Workup

  1. additionwas added slowly dropwise
  2. additionAfter addition
  3. concentrationThe product mixture was concentrated under vacuum
  4. customthe residue was triturated with a mixture of heptane/ethyl acetate
  5. customThe white solid precipitated
  6. filtrationwas filtered
  7. customdried under a stream of dry nitrogen

Sources & evidence

ORD record
ord-a4fd72100998485abe94e958322a2d24
Source dataset
uspto-grants-2010_06
Patent number
US07741315B2

Reaction notes

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