Hydrochloric Acid → N-(3,4-Dichlorobenzoyl)glycine

HRID 1351140Notes

Reaction equation

HRID 1351140 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][NH:5][C:6](=[O:15])[C:7]1[CH2:8][C:9](Cl)([Cl:13])[CH:10]=[CH:11][CH:12]=1.[OH-].[Na+].[ClH:19]>>[Cl:13][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[Cl:19])[C:6]([NH:5][CH2:4][C:3]([OH:2])=[O:16])=[O:15]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69512998HCID 69512998, compound

Product 1

HCID 260363N-(3,4-Dichlorobenzoyl)glycineYield 78%

Conditions

Temperature
50 °C

Procedure

(3,3-Dichlorobenzoylamino)acetic acid methyl ester (25.91 g, 100 mmol, 1.0 eq., see step (a) above) was added to the flask followed by aqueous sodium hydroxide (1 M, 198 mL, 200 mmol, 2.0 eq.). The mixture was heated to 50° C. using an oil bath for 2 hours. On cooling, a white precipitate formed. The mixture was cooled further to 5° C. using an ice/water bath. Concentrated hydrochloric acid (60 mL) was added very slowly to the cooled solution, ensuring that the temperature did not rise above 10° C. The mixture was stirred for 10 minutes and was then filtered. The white solid was air dried for 15 minutes and then dried in vacuo at 40° C. for 16 hours to give an off-white solid (19.15 g, 78%).

Workup

  1. customfor 2 hours
  2. temperatureOn cooling
  3. customa white precipitate formed
  4. temperatureThe mixture was cooled further to 5° C.
  5. customdid not rise above 10° C
  6. filtrationwas then filtered
  7. customdried for 15 minutes
  8. customdried in vacuo at 40° C. for 16 hours

Sources & evidence

ORD record
ord-0085e7b499144596b202b20894935e5e
Source dataset
uspto-grants-2007_05
Patent number
US07217708B2

Reaction notes

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