Anthranilic Acid → Bentranil

HRID 628203Notes

Reaction equation

HRID 628203 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14].C(N(CC)CC)C.O>CN(C)C(=O)C>[C:2]1([C:1]2[O:8][C:13](=[O:14])[C:12]3[CH:16]=[CH:17][CH:18]=[CH:19][C:11]=3[N:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 962WaterHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 13926BentranilYield 81.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent2×

Procedure

In a 500 ml three-necked flask provided with magnetic stirrer, reflux condenser, drying tube and dropping funnel, 2.81 g (20 mmol) of benzoyl chloride were dissolved in 50 ml of N,N-dimethylacetamide and 2.74 g (20 mmol) of 2-aminobenzoic acid as powder were added thereto while stirring. A mixture of 2.02 g (20 mmol) of triethylamine and 5 ml of N,N-dimethylacetamide were subsequently slowly added dropwise at room temperature. After stirring at room temperature for 1 hour, 200 ml of water were added and the precipitate formed was filtered off with suction, washed with water and dried at 80° C. under reduced pressure. The product was then heated in 50 ml of acetic anhydride under reflux for 2 hours. After cooling, the precipitate formed was filtered off with suction and washed with acetic acid and then with water. Recrystallization from n-hexane gave 3.65 g of product.

Workup

  1. customIn a 500 ml three-necked flask provided with magnetic stirrer
  2. temperaturereflux condenser
  3. customdrying tube
  4. additionwere subsequently slowly added dropwise at room temperature
  5. stirringAfter stirring at room temperature for 1 hour
  6. customthe precipitate formed
  7. filtrationwas filtered off with suction
  8. washwashed with water
  9. customdried at 80° C. under reduced pressure
  10. temperatureThe product was then heated in 50 ml of acetic anhydride
  11. temperatureunder reflux for 2 hours
  12. temperatureAfter cooling
  13. customthe precipitate formed
  14. filtrationwas filtered off with suction
  15. washwashed with acetic acid
  16. customRecrystallization from n-hexane

Sources & evidence

ORD record
ord-d47ffe22eb6b415c897c4de82d04add4
Source dataset
uspto-grants-2016_04
Patent number
US09312043B2

Reaction notes

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