Chloroacetic Acid → HCID 14859098, compound

HRID 239005Notes

Reaction equation

HRID 239005 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[CH2:13][C:14]([OH:16])=[O:15].CCOCC.Cl>C([O-])([O-])=O.[Na+].[Na+].C(OCC)(=O)C.CO>[C:14]([CH2:13][NH:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])([OH:16])=[O:15]

Participants

7

Reactant 4

HCID 300Chloroacetic AcidHCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 124762-Amino-5-chlorobenzoic acid

Product 1

HCID 14859098HCID 14859098, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 10340Sodium CarbonateSolvent2×HCID 21584119Ethylacetate methanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-amino-5-chlorobenzoic acid (2.0 g, 11.6 mmol) in 15 ml of 2 N Na2CO3, a solution of chloroacetic acid (0.69 g, 7.3 mmol) in 7.5 ml of 2 N Na2CO3 was added dropwise. After stirred for 20 hours at 80° C., the reaction mixture was cooled down to room temperature. 50 ml ether and 8 ml of 2 N hydrochloric acid were added to the mixture. The organic phase was separated, and dried with MgSO4. After concentration, a light brown solid was obtained. A white solid (2-(N-carboxymethylamino)-5-chlorobenzoic acid) (1.58 g, yield: 59%; mp: 182-183° C.) was obtained through silica gel column chromatography (ethyl acetate/methanol, v/v, 1/1).

Workup

  1. temperaturethe reaction mixture was cooled down to room temperature
  2. customThe organic phase was separated
  3. dry with materialdried with MgSO4
  4. concentrationAfter concentration
  5. customa light brown solid was obtained

Sources & evidence

ORD record
ord-3a3c68be2d3e44559c8a9f2ac9052deb
Source dataset
uspto-grants-2014_02
Patent number
US08642765B2

Reaction notes

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