3-Aminobenzamide → HCID 20564280, compound

HRID 848737Notes

Reaction equation

HRID 848737 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([NH2:7])=[O:6].Cl[CH2:12][C:13]([O:15][CH3:16])=[O:14].C(=O)([O-])[O-].[Ca+2]>CN(C)C=O>[CH3:16][O:15][C:13](=[O:14])[CH2:12][NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5](=[O:6])[NH2:7])[CH:3]=1

Participants

5

Reactant 3

HCID 16453-AminobenzamideHCID 7295Methyl chloroacetateHCID 10112Calcium Carbonate

Product 1

HCID 20564280HCID 20564280, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 6.8 g of 3-aminobenzamide, 5.5 g of methyl monochloroacetate and 10.0 g of calcium carbonate was added 30 ml of dimethylformamide and the mixture was stirred at 110° to 120° C. for 2 hours. The inorganic salt precipitated was filtered off and the filtrate was concentrated under reduced pressure. 50 ml of water was added to the resulting residue and the mixture was stirred to precipitate crystals. The crystals were collected by filtration, dried and recrystallized from a mixture of methanol and diethyl ether to obtain 5.7 g of N-(3-carbamoylphenyl)glycine methyl ester as colorless needles having a melting point of 146°-147° C.

Workup

  1. customThe inorganic salt precipitated
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. addition50 ml of water was added to the resulting residue
  5. stirringthe mixture was stirred
  6. customto precipitate crystals
  7. filtrationThe crystals were collected by filtration
  8. customdried
  9. customrecrystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-d131304facaa4f75a93dc596b4b6bdb7
Source dataset
uspto-grants-1981_10
Patent number
US04297357

Reaction notes

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