O-Phenylenediamine → HCID 19915239, compound

HRID 1090345Notes

Reaction equation

HRID 1090345 reaction equation
C[Si](OP(=O)=O)(C)C.[Br:9][C:10]1[CH:11]=[C:12]([C:26](O)=O)[C:13]([C:16]2[C:17](=[CH:21][C:22]([Br:25])=[CH:23][CH:24]=2)[C:18](O)=O)=[CH:14][CH:15]=1.[C:29]1([NH2:36])[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH2:35].C([O-])(O)=O.[Na+]>>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:17]=2[C:18]2[NH:35][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[N:36]=2)=[C:12]([C:26]2[NH:35][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[N:36]=2)[CH:11]=1

Participants

5

Reactant 4

HCID 7243O-PhenylenediamineHCID 516892Sodium BicarbonateHCID 12808220HCID 12808220, compoundHCID 16133246Trimethyl(phosphooxy)silane

Product 1

HCID 19915239HCID 19915239, compoundYield 53.9%

Conditions

Temperature
160 °C

Procedure

To the PPSE solution was added 15.0 g of 4,4'-dibromodiphenic acid, 8.11 g of o-phenylene diamine (recrystallized from methylene chloride and charcoal). This mixture was rapidly heated to 160° C. and maintained there for 20 hours. The solution was cooled, then poured into 2 1 of 10% NaHCO3 solution. The product was filtered, washed with 300 ml of hot methylene chloride, then extracted using a Soxhlet extractor using 10% NaHCO3 overnight. The product was dried then recrystallized from ethanol to give 11 g of white crystals, mp 326° C.-328° C. Analysis calculated for C26H16N4Br2 : C, 57.38; H, 2.96; N, 10.29. Found: C, 57.81; H, 3.04, N, 10.30.

Workup

  1. temperaturemaintained there for 20 hours
  2. temperatureThe solution was cooled
  3. filtrationThe product was filtered
  4. washwashed with 300 ml of hot methylene chloride
  5. extractionextracted
  6. custom10% NaHCO3 overnight
  7. customThe product was dried
  8. customthen recrystallized from ethanol

Sources & evidence

ORD record
ord-dcdfa938f8984f43aed2c0c0475c4db7
Source dataset
uspto-grants-1992_01
Patent number
US05081256

Reaction notes

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