1,1'-Carbonyldiimidazole → 5-(Morpholin-4-yl)-1,3-dihydro-benzimidazol-2-one

HRID 884428Notes

Reaction equation

HRID 884428 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]([NH2:14])[C:10]([NH2:13])=[CH:11][CH:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16]>O1CCCC1>[N:1]1([C:7]2[CH:12]=[CH:11][C:10]3[NH:13][C:15](=[O:16])[NH:14][C:9]=3[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 141123324-(Morpholin-4-yl)benzene-1,2-diamine

Product 1

HCID 588051685-(Morpholin-4-yl)-1,3-dihydro-benzimidazol-2-oneYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of crude 4-morpholin-4-yl-benzene-1,2-diamine (0.75 g, 3.9 mmol) in tetrahydrofuran (4 mL) was treated dropwise with a solution of carbonyldiimidazole (0.76 g, 4.7 mmol) in tetrahydrofuran (12 mL). The reaction mixture was stirred for 16 h at room temperature, and the solid product was collected by filtration and recrystallized from ethanol to afford the white solid product (0.47 g, 55%). See, J. Am. Chem., Soc., 118:4018 (1996).

Workup

  1. filtrationthe solid product was collected by filtration
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-78ca1f94fa5b43dfa64a4cf9b10fb67c
Source dataset
uspto-grants-2012_08
Patent number
US08242115B2

Reaction notes

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