Fomesafen → HCID 14880456, compound

HRID 2166382Notes

Reaction equation

HRID 2166382 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[O:28])[C:7]1[CH:12]=[C:11]([O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][C:15]=2[Cl:24])[CH:10]=[CH:9][C:8]=1[N+:25]([O-:27])=[O:26])(=[O:4])=[O:3].C[C:30]([CH3:33])([O-:32])[CH3:31].[K+]>O1CCCC1.C1(C)C=CC=CC=1>[Cl:24][C:15]1[CH:16]=[C:17]([C:20]([F:21])([F:23])[F:22])[CH:18]=[CH:19][C:14]=1[O:13][C:11]1[CH:10]=[CH:9][C:8]([N+:25]([O-:27])=[O:26])=[C:7]([CH:12]=1)[C:6]([N:5]([C:6](=[O:28])[C:7]1[CH:33]=[C:30]([O:32][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:16][C:15]=2[Cl:24])[CH:31]=[CH:9][C:8]=1[N+:25]([O-:27])=[O:26])[S:2]([CH3:1])(=[O:4])=[O:3])=[O:28]

Participants

5

Reactant 2

HCID 51556FomesafenHCID 23665647Potassium tert-butoxide

Product 1

HCID 14880456HCID 14880456, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To N-methylsulfonyl-5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitro-benzamide (20.0 grams, 45.6 millimoles) dissolved in 100 ml tetrahydrofuran was added potassium tertiary butoxide in tetrahydrofuran with cooling. A solution of the acid chloride product as described in Example 1 in tetrahydrofuran was then added and the mixture stirred at ambient temperature for forty eight hours under nitrogen with precautions taken to exclude moisture throughout this procedure. The mixture was then diluted with toluene, washed three times with water and saturated sodium chloride solution. The organic phase was concentrated by vacuum to dryness. The residue was shaken with toluene then reconcentrated three times. The final residue was covered with toluene, shaken, the insolubles filtered off, and washed several more times with toluene and hexane. The material was triturated for 30 minutes by stirring with 50 ml hexane. The insolubles were filtered off and dried. The material was purified further by trituration with 5% potassium carbonate followed by drying and recrystallization from toluene/hexane mixtures. The desired product had a melting point of 165.5°-167.5° C.

Workup

  1. temperaturewith cooling
  2. additionwas then added
  3. washwashed three times with water and saturated sodium chloride solution
  4. concentrationThe organic phase was concentrated by vacuum to dryness
  5. stirringThe residue was shaken with toluene
  6. stirringshaken
  7. filtrationthe insolubles filtered off
  8. washwashed several more times with toluene and hexane
  9. customThe material was triturated for 30 minutes
  10. stirringby stirring with 50 ml hexane
  11. filtrationThe insolubles were filtered off
  12. customdried
  13. customThe material was purified further by trituration with 5% potassium carbonate
  14. customby drying
  15. customrecrystallization from toluene/hexane mixtures

Sources & evidence

ORD record
ord-6c710514e6bc4cd2a7076599626152f0
Source dataset
uspto-grants-1990_07
Patent number
US04945113

Reaction notes

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