Benzyl azide → HCID 68990558, compound

HRID 240766Notes

Reaction equation

HRID 240766 reaction equation
[CH2:1]([N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14])[C:2]#[CH:3].[CH2:15]([Sn:19]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:23][CH2:24][CH2:25][CH3:26])N(C)C)[CH2:16][CH2:17][CH3:18].[CH2:31]([N:38]=[N+:39]=[N-:40])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CCCCCC>[CH2:31]([N:38]1[C:2]([CH2:1][N:4]2[C:8](=[O:9])[C:7]3[C:6](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]2=[O:14])=[C:3]([Sn:19]([CH2:15][CH2:16][CH2:17][CH3:18])([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:27][CH2:28][CH2:29][CH3:30])[N:40]=[N:39]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 12152Benzyl azideHCID 81644N-prop-2-ynylphthalimideHCID 11034994Dimethylaminotri-n-butyltin

Product 1

HCID 68990558HCID 68990558, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
70 °C

Procedure

N-Propargylphthalimide (2.35 g mg, 12.7 mmol) was added to 1,1,1-tributyl-N,N-dimethylstannanamine (4.23 mg, 12.7 mmol) in hexane (3.0 mL) and stirred in a sealed vial at 70° C. for 2 hours. The mixture was cooled to ambient temperature and the vial was stirred unsealed for 10 minutes. Benzyl azide (2.0 mL, 16.0 mmol) was added and the vial was resealed and heated to 130° C. overnight. The mixture was purified by silica gel chromatography eluting with a gradient of 10-50% ethyl acetate in hexanes to afford the title compound. MS (ESI+) m/z 609.3 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. stirringthe vial was stirred unsealed for 10 minutes
  3. temperatureheated to 130° C. overnight
  4. customThe mixture was purified by silica gel chromatography
  5. washeluting with a gradient of 10-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-4e672f7ca4f141aea9d65471bf205c1e
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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