Dichloromethane → HCID 38901236, compound

HRID 491885Notes

Reaction equation

HRID 491885 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 N-benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide (8.02 g, 27.2 mmol) in acetonitrile (100 mL) was achieved by heating to reflux. After the reaction mixture was cooled to 0° C., NaN3 (2.30 g, 35.4 mmol) and trifluoromethanesulfonic anhydride (10 g, 35.4 mmol) were added. The reaction mixture was then stirred at room temperature overnight. Dichloromethane (200 mL) was added. The reaction mixture was extracted with saturated sodium bicarbonate solution three times and brine one time and then was 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. extractionThe reaction mixture was extracted with saturated sodium bicarbonate solution three times and brine one time
  3. dry with materialwas dried over MgSO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7072b8ab07d445eca55f9a69658737c3
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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