Chloroacetic Acid → N-(2-carbamoyl-5-chlorophenyl)glycine

HRID 848736Notes

Reaction equation

HRID 848736 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Cl[CH2:13][C:14]([OH:16])=[O:15].[I-].[Na+].[O-2].[Mg+2].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[C:4]([C:3]1[CH:7]=[CH:8][C:9]([Cl:11])=[CH:10][C:2]=1[NH:1][CH2:13][C:14]([OH:16])=[O:15])(=[O:5])[NH2:6]

Participants

7

Reactant 5

HCID 300Chloroacetic AcidHCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 6850729Magnesium monoxideHCID 123748372-Amino-4-chlorobenzamide

Product 1

HCID 20564281N-(2-carbamoyl-5-chlorophenyl)glycineYield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 0.34 g of 2-amino-4-chlorobenzamide, 0.57 g of monochloroacetic acid, 0.90 g of sodium iodide and 0.24 g of magnesium oxide was added 2 ml of dimethylformamide and the mixture was stirred at a temperature between 90° and 100° C. for 2.5 hours. After cooling, the reaction mixture was poured into 50 ml of a 2.6% aqueous sodium carbonate solution. The resulting precipitates were filtered off and the filtrate was extracted with 50 ml of chloroform. The aqueous layer was acidified with concentrated hydrochloric acid to precipitate crystals. The crystals were collected by filtration and recrystallized from aqueous methanol to obtain 0.20 g of N-(2-carbamoyl-5-chlorophenyl)glycine as needles having a melting point of 217°-222° C. (decomposition).

Workup

  1. temperatureAfter cooling
  2. customThe resulting precipitates
  3. filtrationwere filtered off
  4. extractionthe filtrate was extracted with 50 ml of chloroform
  5. customto precipitate crystals
  6. filtrationThe crystals were collected by filtration
  7. customrecrystallized from aqueous methanol

Sources & evidence

ORD record
ord-7002ce446fd64ce19002bac45cd0ba21
Source dataset
uspto-grants-1981_10
Patent number
US04297357

Reaction notes

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