Acetonitrile → 4-(Trifluoromethoxy)benzoyl azide

HRID 1388366

Reaction equation

HRID 1388366 reaction equation
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8](F)=[O:9])=[CH:6][CH:5]=1.[N-:15]=[N+:16]=[N-:17].[Na+].C1OCCOCCOCCOCCOCCOC1.C(#N)C>C(OCC)C>[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:15]=[N+:16]=[N-:17])=[O:9])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 2855718-Crown-6HCID 33557Sodium AzideHCID 67612Benzoyl fluoride, 4-(trifluoromethoxy)-

Product 1

HCID 132813144-(Trifluoromethoxy)benzoyl azide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5 grams (24 mmol) of 4-(trifluoromethoxy)benzoyl fluoride, 1.87 grams (29 mmol) of sodium azide, 0.2 grams of 18-Crown-6 ether, and 20 ml. of acetonitrile was stirred at room temperature for two hours under an atmosphere of dry nitrogen. The reaction mixture was diluted with diethyl ether, filtered and concentrated under reduced pressure, with a bath temperature of 40° C., to give the title compound as a turbid oil. IR showed adsorptions at 2280, 2240 and 1695 cm-1.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure, with a bath temperature of 40° C.

Sources & evidence

ORD record
ord-f79fc335e7344fa0a0035b33648b6dbd
Source dataset
uspto-grants-1984_02
Patent number
US04431667

Linked notes

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