Acetic Acid → HCID 20295989, compound

HRID 1389938Notes

Reaction equation

HRID 1389938 reaction equation
[C:1]([CH:4]([NH:12][C:13]1[C:14]([Cl:24])=[CH:15][C:16]([Cl:23])=[C:17]([CH:22]=1)[C:18]([O:20]C)=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])(=[O:3])N.Cl.C(O)(=[O:28])C>>[C:18]([C:17]1[C:16]([Cl:23])=[CH:15][C:14]([Cl:24])=[C:13]([NH:12][CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[Cl:11])[C:1]([OH:28])=[O:3])[CH:22]=1)([OH:20])=[O:19]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 20296007HCID 20296007, compound

Product 1

HCID 20295989HCID 20295989, compound

Procedure

A mixture of 43 parts of methyl 5-(α-carbamoyl-o-chlorobenzylamino)-2,4-dichlorobenzoate, 400 parts of a hydrochloric acid solution and 200 parts of glacial acetic acid is stirred and refluxed for 70 hours. The reaction mixture is cooled and the precipitated product is filtered off. It is washed on the filter with fresh water and then dissolved in ether. The ethereal solution is shaken with water and with alkaline water. The aqueous phase is separated, acidified with a hydrochloric acid solution and the product is extracted with ether. The latter is washed twice with water, dried, filtered and evaporated, yielding 34.1 parts of N-(5-carboxy-2,4-dichlorophenyl)-2-(o-chlorophenyl)glycine as a solid residue; mp. 210° C.

Workup

  1. temperaturerefluxed for 70 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationthe precipitated product is filtered off
  4. washIt is washed on the
  5. filtrationfilter with fresh water
  6. dissolutiondissolved in ether
  7. stirringThe ethereal solution is shaken with water and with alkaline water
  8. customThe aqueous phase is separated
  9. extractionthe product is extracted with ether
  10. washThe latter is washed twice with water
  11. customdried
  12. filtrationfiltered
  13. customevaporated

Sources & evidence

ORD record
ord-5cc9a8c205c143c39512c6c98749a10f
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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