Water → HCID 23451868, compound

HRID 857913Notes

Reaction equation

HRID 857913 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6](C(O)=O)=[CH:5][N:4]=1.C1(P([N:28]=[N+:29]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C([N:33]([CH2:36]C)CC)C.[OH2:38]>C1(C)C=CC=CC=1>[F:13][C:2]([F:1])([F:12])[C:3]1[CH:11]=[C:10]([C:36]([N:33]=[N+:28]=[N-:29])=[O:38])[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 27775516-(Trifluoromethyl)nicotinic acid

Product 1

HCID 23451868HCID 23451868, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 6-trifluoromethylnicotinic acid (2.90 g) in toluene (130 mL) was treated with diphenylphosphoryl azide (3.30 mL), then triethylamine (2.30 mL). After stirring at room temperature for 3.5 hours the reaction mixture was treated with water (80 mL). The organic phase was separated and the aqueous phase further extracted three times with ethyl acetate (40 mL). The combined organics were dried over magnesium sulfate and then evaporated under reduced pressure at room temperature such as to give the title compound as a 0.3M solution in toluene, which was used without further purification.

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous phase further extracted three times with ethyl acetate (40 mL)
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. customevaporated under reduced pressure at room temperature such as

Sources & evidence

ORD record
ord-88a623b6e45c423e89510c2d79b29400
Source dataset
uspto-grants-2006_12
Patent number
US07148215B2

Reaction notes

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