Sodium Azide → HCID 22106522, compound

HRID 1456315Notes

Reaction equation

HRID 1456315 reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:31]([CH:33]2[CH2:35][CH2:34]2)=O)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[N-:36]=[N+:37]=[N-:38].[Na+].C(=O)([O-])O.[Na+]>C(#N)C>[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[C:31]([CH:33]3[CH2:35][CH2:34]3)=[N:38][N:37]=[N:36]2)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 748373HCID 748373, compound

Product 1

HCID 22106522HCID 22106522, compoundYield 14.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trifluoromethane sulfonic anhydride (9.42 ml) was added dropwise over 10 min to a solution of cyclopropanecarboxylic acid(4-benzyloxy-phenyl)-amide (15 g) and sodium azide (3.64 g) in acetonitrile (250 ml) at 0°. The reaction mixture was stirred at room temperature under nitrogen for 16 h. 10% Aqueous sodium hydrogen carbonate (80 ml) was added and the organic layer was separated. The aqueous layer was further extracted with ethyl acetate (2×100 ml). The combined organic parts were dried over anhydrous sodium sulphate and concentrated in vacuo to give a brown oil. Purification by chromatography with ethyl acetate:isohexane (1:1) as eluant afforded the title compound (2.4 g) as a yellow solid, m.p. 118°.

Workup

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was further extracted with ethyl acetate (2×100 ml)
  3. dry with materialThe combined organic parts were dried over anhydrous sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customto give a brown oil
  6. customPurification by chromatography with ethyl acetate:isohexane (1:1) as eluant

Sources & evidence

ORD record
ord-664194060c5b4ad98def5f8d51ae2a51
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

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