Ethylene Glycol → HCID 67263900, compound

HRID 1041491Notes

Reaction equation

HRID 1041491 reaction equation
[CH:1]([C:3]1[N:4]([C:8]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH:5]=[CH:6][N:7]=1)=[O:2].[CH2:19](O)[CH2:20][OH:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1.[OH-].[Na+]>>[O:2]1[CH2:19][CH2:20][O:21][CH:1]1[CH:3]1[NH:7][CH2:6][CH2:5][N:4]1[C:8]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:9]=1[C:10]#[N:11]

Participants

6

Reactant 5

HCID 174Ethylene GlycolHCID 241BenzeneHCID 14798Sodium HydroxideHCID 521998p-Toluenesulfonic acid monohydrateHCID 86634051HCID 86634051, compound

Product 1

HCID 67263900HCID 67263900, compoundYield 66%

Procedure

Into a round bottom flask equipped with a Dean Stark trap, 2-(2-formyl-imidazol-1-yl)-4-nitro-benzonitrile (10.48 g, 0.04327 mol), 1,2-ethanediol (15.0 mL, 0.269 mol), p-toluenesulfonic acid monohydrate (8.23 g, 0.0433 mol), and benzene (150 mL, 1.7 mol) were added. The reaction was heated to reflux for 6 hours. The reaction was cooled to room temperature. 1N NaOH was added to adjust the pH to 10. The reaction was partitioned with water and EtOAc. The organic was separated, washed with Brine, and dried over magnesium sulfate. The solid was filtered and washed with EtOAc. The solvent was removed under vacuum. The product was isolated via ISCO column chromatography with DCM and methanol as eluant (0 to 5% methanol). The collected fractions afforded 2-(2-[1,3]dioxolan-2-yl-imidazolidin-1-yl)-4-nitro-benzonitrile as a yellow solid (8.20 g, 66%). 1H-NMR (DMSO-D6, 400 MHz): δ8.53 (d, 1H), 8.42 (s, 1H), 8.35 (d, 1H), 7.65 (s, 1H), 7.14 (s, 1H), 5.82 (s, 1H), 3.65 (bs, 2H), 3.45 (bs, 2H).

Workup

  1. additionwere added
  2. temperatureThe reaction was heated
  3. temperatureto reflux for 6 hours
  4. customThe reaction was partitioned with water and EtOAc
  5. customThe organic was separated
  6. washwashed with Brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe solid was filtered
  9. washwashed with EtOAc
  10. customThe solvent was removed under vacuum
  11. customThe product was isolated via ISCO column chromatography with DCM and methanol as eluant (0 to 5% methanol)

Sources & evidence

ORD record
ord-cc211f5ef5b442439beb22316d3ef15c
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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