Triethylamine → HCID 66801817, compound

HRID 2206202Notes

Reaction equation

HRID 2206202 reaction equation
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)[O:3]1.C(N(CC)CC)C.Cl[CH2:25][CH2:26][N:27]=[C:28]=[O:29].CC(C)([O-])C.[K+]>C1COCC1.O>[CH3:8][C:6]1([CH3:7])[C:2]([CH3:16])([CH3:1])[O:3][B:4]([C:9]2[CH:15]=[CH:14][C:12]([N:13]3[CH2:25][CH2:26][NH:27][C:28]3=[O:29])=[CH:11][CH:10]=2)[O:5]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 23665647Potassium tert-butoxide

Product 1

HCID 66801817HCID 66801817, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.05 g) and triethylamine (1.34 mL) in THF (20 mL) was added 1-chloro-2-isocyanatoethane (0.409 mL) at 0° C., and the mixture was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give a powder. A mixture of the obtained powder and potassium tert-butoxide (1.08 g) in THF (20 mL) was stirred overnight at room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was crystallized from ethyl acetate and diisopropyl ether to give the title compound (0.98 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give a powder
  6. stirringwas stirred overnight at room temperature
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed with saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe obtained residue was crystallized from ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-8fe750a28a454fc5a658c2639bc245f5
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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