Hydrochloric Acid → HCID 21427654, compound

HRID 437980Notes

Reaction equation

HRID 437980 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:6][C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14])[CH3:5].CN(C)C=O.[Cl:21][CH2:22][C:23](Cl)=[O:24].Cl>ClC1C=CC=CC=1>[CH3:1][O:2][C:3]([CH:4]([N:6]([C:23](=[O:24])[CH2:22][Cl:21])[C:7]1[C:12]([Cl:13])=[CH:11][CH:10]=[CH:9][C:8]=1[Cl:14])[CH3:5])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6577Chloroacetyl chlorideHCID 54158568HCID 54158568, compound

Product 1

HCID 21427654HCID 21427654, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

18.4 g of α-(2,6-dichloroanilino)-propionic acid methyl ester, 1 ml of dimethylformamide and 100 ml of chlorobenzene are heated to 100° (internal temperature). An addition is made dropwise at this temperature, with stirring, of 8 ml of chloroacetyl chloride. After the evolution of HCl has ceased, stirring is maintained for 1 hour at 130°-140° bath temperature. The reaction mixture is allowed to cool to room temperature, the solvent is removed in a rotary evaporator, and the yellow oil remaining as residue is crystallised from diisopropyl ether. There is obtained 16 g of final product having a melting point of 82°-85° (Compound No. 10).

Workup

  1. additionAn addition
  2. temperatureis maintained for 1 hour at 130°-140° bath temperature
  3. customthe solvent is removed in a rotary evaporator
  4. customis crystallised from diisopropyl ether

Sources & evidence

ORD record
ord-38d3db97a5ab42faa3daa3ac558e7191
Source dataset
uspto-grants-1977_06
Patent number
US04032657

Reaction notes

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