1,2-Phenylenediamine dihydrochloride → HCID 18407015, compound

HRID 1016437

Reaction equation

HRID 1016437 reaction equation
Cl.Cl.[C:3]1([NH2:10])[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH2:9].[CH3:11][CH:12]1[CH2:17][CH2:16][O:15][C:13]1=O>Cl>[NH:9]1[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[N:10]=[C:11]1[CH:12]([CH3:13])[CH2:17][CH2:16][OH:15]

Participants

4

Reactant 2

HCID 119901,2-Phenylenediamine dihydrochlorideHCID 98323alpha-Methylbutyrolactone

Product 1

HCID 18407015HCID 18407015, compoundYield 126.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Following the general procedure described in A. R. Friedman, D. S. Payne and A. R. Day, J. Heterocyclic Chemistry, 3:257-259(1966), a mixture of 9 g of 1,2-phenylenediamine dihydrochloride and 7 g of 2-methylbutyrolactone in 60 mL of 4N hydrochloric acid was heated to reflux for 4 days, 1 teaspoon of decolorizing carbon added, and after another 15 min reflux, filtered hot. The filtrate was concentrated under reduced pressure to near dryness, the residue 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, 12 g of 3-(1H-benzimidazol-2-yl)-butan-1-ol was obtained as a resin.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 4 days
  3. addition1 teaspoon of decolorizing carbon added
  4. temperatureafter another 15 min reflux
  5. filtrationfiltered hot
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. extractionextracted into 3×100 mL of ethyl acetate
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customAfter drying under vacuum

Sources & evidence

ORD record
ord-c3402856b1b044e9a112a35d3f7211ca
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Linked notes

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