Chloroacetic Acid → N,N-Diethylglycine

HRID 1516136

Reaction equation

HRID 1516136 reaction equation
Cl[CH2:2][C:3]([OH:5])=[O:4].[CH2:6]([NH:8][CH2:9][CH3:10])[CH3:7]>>[CH2:6]([N:8]([CH2:2][C:3]([OH:5])=[O:4])[CH2:9][CH3:10])[CH3:7]

Participants

3

Reactant 2

HCID 300Chloroacetic AcidHCID 8021Diethylamine

Product 1

HCID 74151N,N-DiethylglycineYield 104.8%

Procedure

A solution of chloroacetic acid (30 g, 0.32 mol) in diethylamine (230 mL, 2.2 mol) was stirred overnight. The obtained white precipitate was removed by filtration. The filtrate was evaporated to dryness to afford yellow oil to which EtOAc (300 mL) was added. The obtained precipitate was again removed by filtration. The filtrate was evaporated to afford yellow solid residue (44 g) that was washed with hexane (2×100 mL), EtOAc (2×50 mL) and again with hexane (50 mL), and then dried in vacuo to afford title Intermediate 2 (38 g).

Workup

  1. customThe obtained white precipitate was removed by filtration
  2. customThe filtrate was evaporated to dryness
  3. customto afford yellow oil to which EtOAc (300 mL)
  4. additionwas added
  5. customThe obtained precipitate was again removed by filtration
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-c050af519d4d4415a82bd6b1297327ed
Source dataset
uspto-grants-2012_07
Patent number
US08227428B2

Linked notes

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