Dichloromethane → HCID 38901236, compound

HRID 2088853Notes

Reaction equation

HRID 2088853 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-5d55bcec727144eba67d5943320585a3
Source dataset
uspto-grants-2013_05
Patent number
US08436006B2

Reaction notes

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