Dichloromethane → HCID 38901236, compound

HRID 390287Notes

Reaction equation

HRID 390287 reaction equation
[CH2:1]([NH:8][C:9](=O)[CH2:10][N:11]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]1=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.ClCCl>C(#N)C>[CH2:1]([N:8]1[C:9]([CH2:10][N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])=[N:25][N:24]=[N:23]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 277803N-benzyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetamide

Product 1

HCID 38901236HCID 38901236, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Dissolution of the white solid isolated in Step A (8.02 g, 27.2 mmol) in acetonitrile (100 mL) was achieved by heating to reflux. After the solution was cooled to 0° C., NaN3 (2.30 g, 35.4 mmol) and trifluoromethanesulfonic anhydride (10 g, 35.4 mmol) were added. The resulting solution was then stirred at room temperature overnight. Dichloromethane (200 mL) was added. The resulting solution was washed with saturated sodium bicarbonate solution three times and brine one time and then dried over MgSO4. The solution was filtered and concentrated to yield 2-(1-benzyl-1H-tetrazol-5-ylmethyl)-isoindole-1,3-dione as a white solid.

Workup

  1. temperatureby heating to reflux
  2. washThe resulting solution was washed with saturated sodium bicarbonate solution three times and brine one time
  3. dry with materialdried over MgSO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-40d49323e06b4232914e94b6b8e3d121
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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