Triethylamine → HCID 18355038, compound

HRID 1533778Notes

Reaction equation

HRID 1533778 reaction equation
[N+:1]([C:4]1[C:5]([NH2:11])=[C:6]([NH2:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH:19]1[CH:24]=[C:23]2[C:25]([N:27]([CH2:30][C:31](Cl)=O)[C:28](=[O:29])[C:22]2=[CH:21][CH:20]=1)=[O:26]>ClCCl>[C:25]1(=[O:26])[N:27]([CH2:30][C:31]2[NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]=3[N:11]=2)[C:28](=[O:29])[C:22]2=[CH:21][CH:20]=[CH:19][CH:24]=[C:23]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 43595253-Nitro-1,2-phenylenediamine

Product 1

HCID 18355038HCID 18355038, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-nitro-1,2-phenylenediamine (1.0 g) and triethylamine (793 mg) in dichloromethane (3 ml) under nitrogen was added portionwise phthalylglycyl chloride (1.61 g) in ice water bath and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was washed with saturated sodium bicarbonate aqueous solution, dried over magnesium sulfate and evaporated in vacuo. To the resulting crude product was added polyphosphoric acid (5 ml) and stirred at 130° C. for 3 hours. After the mixture was cooled at ambient temperature, ammonia solution (28%) was added to the reaction mixture in ice water bath. The precipitate was collected by vacuum filtration to give 2-phthalimidomethyl-4-nitro-1H-benzimidazole (1.35 g).

Workup

  1. washThe reaction mixture was washed with saturated sodium bicarbonate aqueous solution
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. additionTo the resulting crude product was added polyphosphoric acid (5 ml)
  5. stirringstirred at 130° C. for 3 hours
  6. additionammonia solution (28%) was added to the reaction mixture in ice water bath
  7. filtrationThe precipitate was collected by vacuum filtration

Sources & evidence

ORD record
ord-21e54d38b90b4ca38433f3b9c34a30f6
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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