Anthranilamide → HCID 20338276, compound

HRID 1439604Notes

Reaction equation

HRID 1439604 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 alkalline 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-5d7680cc040748b98e9b0508c9bffc66
Source dataset
uspto-grants-1977_11
Patent number
US04060526

Reaction notes

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