1,1'-Carbonyldiimidazole → 5-[2-[2H-1,3-benzooxazine-2,4(3H)-dion-3-yl]ethylthio]imidazo[1,2-a]pyridine

HRID 1081727Notes

Reaction equation

HRID 1081727 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][S:9][C:10]1[N:15]2[CH:16]=[CH:17][N:18]=[C:14]2[CH:13]=[CH:12][CH:11]=1)=[O:5].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>O1CCCC1>[O:1]1[C:2]2[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=2[C:4](=[O:5])[N:6]([CH2:7][CH2:8][S:9][C:10]2[N:15]3[CH:16]=[CH:17][N:18]=[C:14]3[CH:13]=[CH:12][CH:11]=2)[C:23]1=[O:24]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 233629775-[2-[2-(Hydroxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628185-[2-[2H-1,3-benzooxazine-2,4(3H)-dion-3-yl]ethylthio]imidazo[1,2-a]pyridineYield 77.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[2-[2-(hydroxy)benzoylamino]ethylthio]imidazo[1,2-a]pyridine (627 mg, 2.00 mmoles) in dry tetrahydrofuran (30 ml) was added 1,1'-carbonyldiimidazole (649 mg, 4.00 mmoles) and the mixture was stirred at room temperature for 15 hours. After the solvent was distilled off, chloroform was added to the residue, which was washed with water and dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography (eluent:ethyl acetate) to obtain 528 mg of the desired product (77.8%, colorless crystals).

Workup

  1. distillationAfter the solvent was distilled off
  2. additionchloroform was added to the residue, which
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationAfter the solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-a8774755c3ad4ebca874b2db5e22891b
Source dataset
uspto-grants-1996_12
Patent number
US05587383

Reaction notes

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