O-Phenylenediamine → HCID 66602380, compound

HRID 1810726Notes

Reaction equation

HRID 1810726 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)([CH3:14])[CH2:9][CH2:10][C:11](O)=O)=[CH:4][CH:3]=1.[C:22]1([NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH2:28]>P(=O)(O)(O)O>[NH:28]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:29]=[C:11]1[CH2:10][CH2:9][C:8]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)([C:5]1[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=1)[CH3:14]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 671744,4-Bis(4-hydroxyphenyl)valeric acid

Product 1

HCID 66602380HCID 66602380, compound

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Procedure

In a four neck 250 mL reaction kettle equipped with an overhead stirrer, thermocouple, gas inlets adapter and condenser, were charged 30.01 gram 4,4-bis(4-hydroxyphenyl)pentanoic acid (0.1048 moles), 15.17 gram 1,2-phenylenediamine (0.1403 moles) and 150 gram polyphosphoric acid. The mixture was stirred at 250 rpm at room temperature for 15 minutes and heated up to 120° C. under argon atmosphere. The reaction was continued for 3 hours and the product was cooled to room temperature. The product obtained in phosphoric acid solution was isolated by precipitating in water followed by neutralization and filtration. The isolated product was dried in vacuum at 90° C. for 48 hours. The conversion of acid to benzimidazole functionality was confirmed by IR spectroscopy.

Workup

  1. customIn a four neck 250 mL reaction kettle
  2. customequipped with an overhead stirrer
  3. temperatureheated up to 120° C. under argon atmosphere
  4. waitThe reaction was continued for 3 hours
  5. temperaturethe product was cooled to room temperature
  6. customwas isolated
  7. customby precipitating in water
  8. filtrationfollowed by neutralization and filtration
  9. customThe isolated product was dried in vacuum at 90° C. for 48 hours

Sources & evidence

ORD record
ord-2b09492b0fc846a8b838ae3ecf2063b8
Source dataset
uspto-grants-2013_01
Patent number
US08362195B2

Reaction notes

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