Chloroacetic Acid → HCID 68144690, compound

HRID 1579738Notes

Reaction equation

HRID 1579738 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]([NH:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])=[O:6].C1(C)C(C)=CC=CC=1.Cl[CH2:32][C:33]([OH:35])=[O:34]>C(N(CC)CC)C>[ClH:22].[C:33]([CH2:32][N:3]([CH3:2])[CH2:4][C:5]([NH:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])=[O:6])([OH:35])=[O:34]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 7237O-XyleneHCID 68141832HCID 68141832, compound

Product 1

HCID 68144690HCID 68144690, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4.6 g of 2-(methylamino-acetamido)-5-chlorobenzophenone hydrochloride were heated in 100 mls. of dry xylene with 3 g of triethylamine and 1.9 g of chloracetic acid for 8 hours under reflux whilst stirring. After cooling, the precipitated triethylamine hydrochloride was filtered off and the filtrate was shaken 3 times with 100 mls. of water each time. After drying over potassium carbonate and filtering, it was concentrated in vacuo, the oily crude base obtained being dissolved in 100 mls. of dry ether and filtered again. By passing in dry hydrogen chloride gas, filtering under suction and drying in a vacuum desiccator, 2.8 g (71% of theory) of 2-(4-carboxy-3-methyl-3-aza-butyramido)-5-chlorobenzophenone hydrochloride were obtained with a melting point of 162°-164°.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated triethylamine hydrochloride was filtered off
  3. stirringthe filtrate was shaken 3 times with 100 mls
  4. dry with materialAfter drying over potassium carbonate
  5. filtrationfiltering
  6. concentrationit was concentrated in vacuo
  7. customthe oily crude base obtained
  8. dissolutionbeing dissolved in 100 mls
  9. filtrationof dry ether and filtered again
  10. filtrationfiltering under suction
  11. customdrying in a vacuum desiccator

Sources & evidence

ORD record
ord-0e367592d187467da8fe88894180bc2c
Source dataset
uspto-grants-1976_01
Patent number
US03931314

Reaction notes

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