Ammonium Chloride → HCID 178521700, compound

HRID 1040447Notes

Reaction equation

HRID 1040447 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][C:11]1([C:14]#[N:15])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:17]=[N+:18]=[N-:19].[Na+].[NH4+].[Cl-]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:16])[NH:10][C:11]1([C:14]2[NH:19][N:18]=[N:17][N:15]=2)[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 57916539HCID 57916539, compound

Product 1

HCID 178521700HCID 178521700, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a round bottom flask was added (1-cyano-cyclopropyl)-carbamic acid benzyl ester (500 mg, 2.31 mmol) in DMF (4 ml), followed by the addition of NaN3 (195 mg, 3 mmol) and NH4Cl (161 mg, 3 mmol). The reaction mixture was stirred at 110° C. for 24 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in EtOAc/water. The organic layer was separated, washed with brine, dried under any. Na2SO4, filtered and concentrated to afford 380 mg of [1-(1H-tetrazol-5-yl)-cyclopropyl]-carbamic acid benzyl ester as a off-white solid, m/z 260.8 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc/water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried under any
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d154f3c93fab4cff9c8d3146c84c67c7
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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