O-Phenylenediamine → SBB045701

HRID 1016440Notes

Reaction equation

HRID 1016440 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1N.[C:9](O)(=O)[CH2:10][CH2:11][CH:12]=[CH2:13].[OH-:16].[NH4+:17]>Cl>[NH:17]1[C:6]2[CH:5]=[CH:4][CH:3]=[CH:2][C:1]=2[N:8]=[C:9]1[CH2:10][CH2:11][CH:12]([OH:16])[CH3:13]

Participants

5

Reactant 3

HCID 7243O-PhenylenediamineHCID 14923Ammonium HydroxideHCID 611384-Pentenoic acid

Product 1

HCID 332756SBB045701

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 8 g of 1,2-phenylenediamine and 6.6 g of 4-pentenoic acid in 50 mL of 4N hydrochloric acid was heated to reflux for 18 hours, cooled in an ice bath, made basic (pH=8) with ammonium hydroxide and extracted into 3×100 mL of ethyl acetate. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. After drying under vacuum, 10 g of 4-(1H-benzimidazol-2-yl)-butan-2-ol was obtained as a thick oil which slowly crystallized.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. temperaturecooled in an ice bath
  4. extractionextracted into 3×100 mL of ethyl acetate
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customAfter drying under vacuum

Sources & evidence

ORD record
ord-7a14ef6d32fd4e27966cd2edf5e7f7b1
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Reaction notes

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