Ethanol → Ethyl 2-(3,4-dichloroanilino)acetate

HRID 2052401Notes

Reaction equation

HRID 2052401 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[NH:5][CH2:6][C:7]([OH:9])=[O:8].[CH2:14](O)[CH3:15].OS(O)(=O)=O>ClC(Cl)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[Cl:13])[NH:5][CH2:6][C:7]([O:9][CH2:14][CH3:15])=[O:8]

Participants

5

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 351250N-(3,4-dichlorophenyl)glycine

Product 1

HCID 2727804Ethyl 2-(3,4-dichloroanilino)acetateYield 78%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 27.5 g (0.125 mol) of 3,4-dichloroanilinoacetic acid, 190 ml of dichloroethane, 15 ml (0.2 mol) of ethanol and 1.5 ml of concentrated H2SO4 is heated for 4 hours under reflux. It is washed with water and with dilute sodium bicarbonate, dried and evaporated to dryness in vacuo. The ester is recrystallised from ethanol and is obtained in a yield of 78%. It melts at 103°-104° C.

Workup

  1. temperatureunder reflux
  2. washIt is washed with water and with dilute sodium bicarbonate
  3. customdried
  4. customevaporated to dryness in vacuo
  5. customThe ester is recrystallised from ethanol
  6. customis obtained in a yield of 78%

Sources & evidence

ORD record
ord-978fa86a46c143c8935faf12bf3f3cbb
Source dataset
uspto-grants-1980_01
Patent number
US04183951

Reaction notes

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