Anthranilamide → HCID 20338276, compound

HRID 1395796Notes

Reaction equation

HRID 1395796 reaction equation
Br.Br.[OH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17]Br)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1.[C:19]([NH2:28])(=[O:27])[C:20]1[C:21](=[CH:23][CH:24]=[CH:25][CH:26]=1)[NH2:22].C([O-])(=O)C.[Na+]>O>[OH:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH:22][C:21]3[CH:23]=[CH:24][CH:25]=[CH:26][C:20]=3[C:19]([NH2:28])=[O:27])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 517045Sodium AcetateHCID 20338299HCID 20338299, compound

Product 1

HCID 20338276HCID 20338276, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 61 g 1-(p-hydroxyphenyl)-4-(2-bromoethyl)piperazine dihydrobromide, 18.5 g anthranilamide, 33.5 g sodium acetate, and 250 ml water was refluxed 16 hours, cooled, filtered and the solid washed with water and isopropanol. The solid was suspended in water and made alkaline with Na2CO3. The solid was filtered, suspended in 75% ethanol and added dilute HCl until acidic. The solution was cooled and the solid filtered and recrystallized from 1200 ml water to give 18.5 g product, m.285.

Workup

  1. temperaturewas refluxed 16 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. washthe solid washed with water and isopropanol
  5. filtrationThe solid was filtered
  6. additionadded dilute HCl until acidic
  7. temperatureThe solution was cooled
  8. filtrationthe solid filtered
  9. customrecrystallized from 1200 ml water

Sources & evidence

ORD record
ord-368db9f74f9d4a1d9f37b488d5aea1fa
Source dataset
uspto-grants-1980_05
Patent number
US04205173

Reaction notes

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