Triethylamine → 1-Isocyanato-1-(trifluoromethyl)cyclopropane

HRID 449444Notes

Reaction equation

HRID 449444 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]1(C(O)=O)[CH2:5][CH2:4]1.C1C=CC(OP([O:23][C:24]2C=CC=CC=2)(N=[N+]=[N-])=O)=CC=1.C([N:32](CC)CC)C>C1(C)C=CC=CC=1>[N:32]([C:3]1([C:2]([F:1])([F:9])[F:10])[CH2:4][CH2:5]1)=[C:24]=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 27783061-(Trifluoromethyl)cyclopropane-1-carboxylic acid

Product 1

HCID 589208171-Isocyanato-1-(trifluoromethyl)cyclopropane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(trifluoromethyl)cyclopropanecarboxylic acid (13 mg, 0.084 mmol) (Oakwood, Cat. #013181), diphenylphosphonic azide (36 uL, 0.17 mmol) and triethylamine (18 uL, 0.13 mmol) in toluene (0.5 mL) was refluxed overnight. The mixture was concentrated under reduced pressure to afford the crude product which was used directly for next step without further purification.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-19dffe7ac8d0477e913320a61f57ba12
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Reaction notes

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