Anthranilamide → 2-[(3-Chloropropyl)amino]benzamide

HRID 1156326Notes

Reaction equation

HRID 1156326 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].Br[CH2:12][CH2:13][CH2:14][Cl:15].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:15][CH2:14][CH2:13][CH2:12][NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 80061-Bromo-3-chloropropaneHCID 10340Sodium Carbonate

Product 1

HCID 196983462-[(3-Chloropropyl)amino]benzamideYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 13.6 parts of 2-aminobenzamide, 31.5 parts of 1-bromo-3-chloropropane, 21 parts of sodium carbonate and 200 parts of ethanol is stirred and refluxed over week-end. The reaction mixture is filtered and the filtrate is evaporated. The oily residue is stirred in methylbenzene. The mixture is filtered till clear and the solvent is evaporated. The oily residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The solid residue is stirred in 2,2'-oxybispropane. The product is filtered off and dried, yielding 7 parts (33%) of 2-[(3-chloropropyl)amino]benzamide; mp. ±100° C.

Workup

  1. temperaturerefluxed over week-end
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. stirringThe oily residue is stirred in methylbenzene
  5. filtrationThe mixture is filtered till clear and the solvent
  6. customis evaporated
  7. customThe oily residue is purified by column-chromatography over silica gel using
  8. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  9. customThe pure fractions are collected
  10. customthe eluent is evaporated
  11. stirringThe solid residue is stirred in 2,2'-oxybispropane
  12. filtrationThe product is filtered off
  13. customdried

Sources & evidence

ORD record
ord-a54b40ad410b4c96a1542011caeba591
Source dataset
uspto-grants-1982_06
Patent number
US04335127

Reaction notes

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