Water → HCID 69020953, compound

HRID 1865065Notes

Reaction equation

HRID 1865065 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9](S(C2C=CC(C)=CC=2)(=O)=O)[C:10]#[N:11])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.[N+:33]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])#[C-:34].O>C1COCC1.CCOC(C)=O>[CH2:39]([O:38][C:36]([C:35]1[NH:33][CH:34]=[C:9]([C:10]#[N:11])[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)=[O:37])[CH3:40]

Participants

7

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetateHCID 3668806HCID 3668806, compound

Product 1

HCID 69020953HCID 69020953, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(4-bromo-phenyl)-2-(toluene-4-sulfonyl)-acrylonitrile (38.76 g, 0.107 mol, prepared directly above) in anhydrous THF (500 mL) is treated with DBU (65.00 mL, 0.434 mol), followed by ethyl isocyanoacetate (25.00 g, 0.214 mol). The resulting dark-brown reaction mixture is allowed to stir at room temperature for 3 hours. The reaction mixture is poured into water (1,000 mL) and extracted with EtOAc (3×250 mL each). The combined organics are washed with 1 N HCl (250 mL), water (250 mL), brine (250 mL), dried over anhydrous Na2SO4, filtered, then concentrated in vacuo to afford an off-white solid. The solid is dissolved in a minimum amount of EtOAc, then treated with excess hexanes, causing a solid to crash out. The solid is recovered by vacuum filtration, washed with hexanes, and dried under vacuum filtration to afford the title compound (23.90 g, 69.9% crude yield) as a off-white solid: 1H NMR (500 MHz; CDCl3) δ 1.22 (t, 3H), 4.26 (q, 2H), 7.39 (d, 2H), 7.45 (d, 1H), 7.55 (d, 2H), 9.70 (bs, 1H).

Workup

  1. extractionextracted with EtOAc (3×250 mL each)
  2. washThe combined organics are washed with 1 N HCl (250 mL), water (250 mL), brine (250 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford an off-white solid
  7. filtrationThe solid is recovered by vacuum filtration
  8. washwashed with hexanes
  9. customdried under vacuum filtration

Sources & evidence

ORD record
ord-41cd7423aab64e7aa81ce258f553ffe5
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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