Sodium Azide → HCID 86590934, compound

HRID 1829059Notes

Reaction equation

HRID 1829059 reaction equation
[O:1]=[C:2]1[C:10](=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]([CH2:20]C(O)=O)[O:12]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[Li]CCCC.[C:29](Cl)(=[O:33])C(Cl)=O.[N-:35]=[N+]=[N-].[Na+]>C1COCC1.CCCCCC.C(Cl)Cl.O.C1(C)C=CC=CC=1>[N:35]([CH2:20][CH:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[NH:3][C:2]2=[O:1])[O:12]1)=[C:29]=[O:33]

Participants

10

Reactant 4

HCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 69659233HCID 69659233, compoundHCID 178418339Butyllithium

Product 1

HCID 86590934HCID 86590934, compoundYield 66%

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of [3-(2-oxo-1,2-dihydro-indol-3-ylidene)-1,3-dihydro-isobenzofuran-1-yl]-acetic acid (200 mg, 0.65 mmol) in THF (8.0 ml) at room temperature was added 2.5M n-BuLi in hexane (272 μl), and the yellow-brown slurry was stirred for 10 minutes. After cooling to 0° C., 2.0M oxalyl chloride in CH2Cl2 (325 μl) was added. The clear orange solution was stirred for 25 minutes, and then sodium azide (51 mg, 0.78 mmol) in water (0.5 ml) was added, followed by addition of water (1 ml). After 20 minutes, the reaction was partitioned between dilute NaHCO3 aqueous solution and CH2Cl2. The CH2Cl2 layer was washed with brine and dried with anhydrous Na2SO4 to give a yellow solution. The solution was diluted with toluene (200 ml), and then rotary evaporated to 100 ml volume. The toluene solution was heated at 90° C. for 40 minutes, cooled to room temperature, and then rotary evaporated to give 3-(3-isocyanatomethyl-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as a yellow oily solid (130 mg, 66%).

Workup

  1. stirringThe clear orange solution was stirred for 25 minutes
  2. waitAfter 20 minutes
  3. customthe reaction was partitioned between dilute NaHCO3 aqueous solution and CH2Cl2
  4. washThe CH2Cl2 layer was washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. customto give a yellow solution
  7. customrotary evaporated to 100 ml volume
  8. temperatureThe toluene solution was heated at 90° C. for 40 minutes
  9. temperaturecooled to room temperature
  10. customrotary evaporated

Sources & evidence

ORD record
ord-e3cee59dd2de4281b50860d04f917b1f
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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