Hydrochloric Acid → 1-Ebio

HRID 2110391Notes

Reaction equation

HRID 2110391 reaction equation
[CH2:1]([NH:3][C:4]1[C:5]([NH2:10])=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].[C:11](N1C=CN=C1)(N1C=CN=C1)=[O:12].C(OCC)(=O)C.Cl>O1CCCC1>[CH2:1]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:10][C:11]1=[O:12])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 902751,2-Benzenediamine, N1-ethyl-

Product 1

HCID 823201-Ebio

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of crude N-ethyl-benzene-1,2-diamine (8.4 g, 62 mmol) in anhydrous tetrahydrofuran (200 mL) was added 1,1′-carbonyldiimidazole (10 g, 62 mmol). The mixture was stirred at room temperature under nitrogen for 12 hours and ethyl acetate (250 mL) followed by a cold 3N aqueous solution of hydrochloric acid (200 mL) were added. The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to afford 1-ethyl-1,3-dihydro-benzimidazol-2-one as a white solid (8.5 g, 69% for three steps). MS (ES) m/z 163.2.

Workup

  1. additionwere added
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f1222526103484f94777a47bd1a2fff
Source dataset
uspto-grants-2009_04
Patent number
US07517899B2

Reaction notes

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