Phthalic Anhydride → 5-[2-[2-(Carboxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridine

HRID 1608600Notes

Reaction equation

HRID 1608600 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1.[C:14]1(=[O:24])[O:19][C:17](=[O:18])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12>C(Cl)(Cl)Cl>[C:17]([C:16]1[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=1[C:14]([NH:1][CH2:2][CH2:3][S:4][C:5]1[N:10]2[CH:11]=[CH:12][N:13]=[C:9]2[CH:8]=[CH:7][CH:6]=1)=[O:24])([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 152293695-[2-(Amino)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628395-[2-[2-(Carboxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridineYield 84.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 5-[2-(amino)ethylthio]imidazo[1,2-a]pyridine (1.12 g, 5.8 mmoles) in chloroform (58 ml) was added phthalic anhydride (1.12 g, 7.56 mmoles) and the mixture was stirred at room temperature for 14 hours and then heated at reflux for 5 hours. The reaction mixture was cooled by standing. The crystals precipitated were filtered off, washed with chloroform and dried to obtain 1.68 g of the desired product (84.8%, colorless crystals).

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. customThe crystals precipitated
  5. filtrationwere filtered off
  6. washwashed with chloroform
  7. customdried

Sources & evidence

ORD record
ord-9f3c16b53d484da2afded576ba717915
Source dataset
uspto-grants-1995_03
Patent number
US05395839

Reaction notes

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