1,1'-Carbonyldiimidazole → 2H-Benzimidazol-2-one, 1,3-dihydro-1-(2-methoxyethyl)-

HRID 1096656Notes

Reaction equation

HRID 1096656 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6]1[C:7]([NH2:12])=[CH:8][CH:9]=[CH:10][CH:11]=1.C1N=CN([C:18](N2C=NC=C2)=[O:19])C=1>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12][C:18]1=[O:19]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 102614521-N-(2-methoxyethyl)benzene-1,2-diamine

Product 1

HCID 99901412H-Benzimidazol-2-one, 1,3-dihydro-1-(2-methoxyethyl)-Yield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The residue 109B (422 mg, 2.54 mmol) was dissolved in THF (7.5 mL). CDI (494 mg, 3.05 mmol) in THF (7.6 mL) was added slowly via addition funnel. After addition the mixture was stirred overnight at room temperature, solvent was removed under vacuum. The residue was purified by column chromatography (5% MeOH/DCM) to give the product 1-(2-methoxyethyl)-1H-benzo[d]imidazol-2(3H)-one (109C) as an orange solid (449 mg, 92%). ESI-MS:m/z 193.3 (M+H)+.

Workup

  1. additionAfter addition the mixture
  2. customsolvent was removed under vacuum
  3. customThe residue was purified by column chromatography (5% MeOH/DCM)

Sources & evidence

ORD record
ord-4ede0777ad9f4c1ba9201627499b8712
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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