Triethylamine → HCID 1883573, compound

HRID 1711148Notes

Reaction equation

HRID 1711148 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Br[CH2:14][C:15]#[N:16].CCN(CC)CC>CN(C=O)C.CCOC(C)=O.[Cl-].[Na+].O>[O:7]=[C:6]1[C:5]2[C:4](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3](=[O:12])[N:2]1[O:1][CH2:14][C:15]#[N:16]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10665N-HydroxyphthalimideHCID 11534Bromoacetonitrile

Product 1

HCID 1883573HCID 1883573, compoundYield 36%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of N-hydroxyphthalimide (5.20 g, 31.88 mmol) in DMF (20 ml) was added bromoacetonitrile (3.0 ml, 45.02 mmol) and Et3N (10.0 ml, 71.8 mmol) and the reaction stirred at room temperature for 2 d. The mixture was diluted with EtOAc (50 ml) and brine (40 ml) and the organic layer was washed with brine (4×20 ml) and 1 N NaOH (30 ml), dried (Na2SO4) and concentrated to afford (1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-acetonitrile (2.3 g, 36%) as a beige solid. 1H NMR (CDCl3) δ 4.96 (s, 2H), 7.80-7.84 (m, 2H), 7.89-7.92 (m, 2H).

Workup

  1. washthe organic layer was washed with brine (4×20 ml) and 1 N NaOH (30 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a9a357e2631d4dce9391f3e967fc5ed5
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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