Water → HCID 178452605, compound

HRID 72397Notes

Reaction equation

HRID 72397 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)#[N:2].[NH4+].[Cl-].[N-:22]=[N+:23]=[N-:24].[Na+].O>CN(C)C=O.C(OC(=O)C)C>[NH:22]1[C:1]([C:3]2[CH:4]=[CH:5][C:6]([C:9]3([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[CH2:10][CH2:11]3)=[CH:7][CH:8]=2)=[N:2][N:24]=[N:23]1

Participants

7

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 58458581HCID 58458581, compound

Product 1

HCID 178452605HCID 178452605, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of tert-butyl (1-(4-cyanophenyl)cyclopropyl)carbamate (D15) (1.5 g, 5.81 mmol) in dimethylformamide (15 ml), NH4Cl (530 mg, 9.90 mmol) was added under nitrogen atmosphere, followed by addition of sodium azide (650 mg, 9.9 mmol). The reaction mixture was heated to 100° C. overnight, then cooled to room temperature with ice-water bath. Water and ethylacetate (100 ml) was added. The organic layer was separated and the solvent was removed. The residue was purified by column chromatography eluting with a mixture petroleum ether/ethyl acetate (1:1). Collected fractions after solvent evaporation afforded the title compound (D16) (830 mg) as a yellow solid.

Workup

  1. temperaturecooled to room temperature with ice-water bath
  2. customThe organic layer was separated
  3. customthe solvent was removed
  4. customThe residue was purified by column chromatography
  5. washeluting with a mixture petroleum ether/ethyl acetate (1:1)
  6. customCollected fractions after solvent evaporation

Sources & evidence

ORD record
ord-131f1d9e4c2b4c859a3d87f36c0fb836
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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