HCID 22096813, compound → 4-N,N-Bis(2-chloroethyl)aminophenoxyacetic acid

HRID 1458692Notes

Reaction equation

HRID 1458692 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:19]=[CH:18][C:11]([O:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7]>Cl>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[CH:19]=[CH:18][C:11]([O:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:10][CH:9]=1)[CH2:5][CH2:6][Cl:7]

Participants

3

Reactant 1

HCID 22096813HCID 22096813, compound

Product 1

HCID 285804-N,N-Bis(2-chloroethyl)aminophenoxyacetic acidYield 64.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 1.99 g (6.50 mmol) of methyl 4-[N,N-bis(2-chloroethyl)amino]phenoxyacetate in 60 ml of concentrated hydrochloric acid was heated at 50° C. for 30 minutes. The suspension was washed with methylene chloride, neutralized with sodium hydrogencarbonate, and then extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then concentrated, whereby 1.23 g of the title compound were obtained as colorless crystals (yield: 65%).

Workup

  1. washThe suspension was washed with methylene chloride
  2. extractionextracted with methylene chloride
  3. washThe extract was washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4b09bf8fbbaf482b97bc396ef2c9cae3
Source dataset
uspto-grants-1998_12
Patent number
US05852011

Reaction notes

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