1-Butanol → 1-(Glycyloxy)butane chloride

HRID 1817299Notes

Reaction equation

HRID 1817299 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].[NH2:2][CH2:3][C:4]([O:6][CH2:11][CH2:12][CH2:13][CH3:14])=[O:5]

Participants

4

Reactant 3

HCID 2631-ButanolHCID 22316Glycine HydrochlorideHCID 24386Thionyl Chloride

Product 1

HCID 866139031-(Glycyloxy)butane chloride

Conditions

Temperature
70 °C

Procedure

To a suspension of glycine hydrochloride (10 g, 89.6 mmol) in 250 mL butanol under nitrogen was added thionyl chloride (45.7 mL, 627 mmol) dropwise. After the addition was complete, the solution was heated at 70° C. overnight. The volatile components were removed on the roto-evaporator and the residue was suspended and evaporated from toluene three times. The resulting crude gum was dissolved in an equal weight of toluene for easy transfer and was used as is in the next reaction.

Workup

  1. additionAfter the addition
  2. customThe volatile components were removed on the roto-evaporator
  3. customevaporated from toluene three times
  4. dissolutionThe resulting crude gum was dissolved in an equal weight of toluene for easy transfer
  5. customas is in the next reaction

Sources & evidence

ORD record
ord-491dd942da334ab9a9e0643ea6bc3180
Source dataset
uspto-grants-2009_10
Patent number
US07598264B2

Reaction notes

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