1-Butanol → Benzimidazole

HRID 1810727Notes

Reaction equation

HRID 1810727 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[CH3:9]N(C)C(=O)C.C(O)CCC.OP(O)(O)=O>C1(C)C=CC=CC=1>[N:7]1[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[NH:8][CH:9]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 1004Phosphoric AcidHCID 7243O-PhenylenediamineHCID 31374Dimethylacetamide

Product 1

HCID 5798Benzimidazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The dried product (5.57 g) obtained from step 1 was charged along with 3.1 grams 1,2-phenylenediamine, 120 mL N,N-dimethyl acetamide, 30 mL n-butanol, 10 grams o-phosphoric acid (85%), and 40 mL toluene in a four neck 250 mL reaction kettle equipped with an overhead stirrer, thermocouple, gas inlets adapter and condenser. The mixture was stirred at 250 rpm at room temperature for 15 minutes and heated to 150° C. under argon atmosphere to remove all the toluene. The reaction was continued for 6 hours and the product was cooled to room temperature.

Workup

  1. customequipped with an overhead stirrer
  2. temperatureheated to 150° C. under argon atmosphere
  3. customto remove all the toluene
  4. waitThe reaction was continued for 6 hours
  5. temperaturethe product was cooled to room temperature

Sources & evidence

ORD record
ord-74ed5e767773497d8ad429ff0279224f
Source dataset
uspto-grants-2013_01
Patent number
US08362195B2

Reaction notes

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