Triphenylphosphine → 2-(Aminomethyl)thiazole-4-carbonitrile

HRID 1745392Notes

Reaction equation

HRID 1745392 reaction equation
[N:1]([CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]#[N:11])[N:9]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[NH2:1][CH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10]#[N:11])[N:9]=1

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 22225783HCID 22225783, compound

Product 1

HCID 101540912-(Aminomethyl)thiazole-4-carbonitrileYield 92.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a magnetically stirred solution of 2-azidomethyl-thiazole-4-carbonitrile (1.3 g, 7.8 mmol) in a mixture of THF (40 mL) and water (4 mL) was added triphenylphosphine (3.10 g, 11.8 mmol) portionwise with ice-bath cooling. After the addition was complete, the mixture was stirred for an additional 18 h at room temperature and extracted with 3% hydrochloric acid (10 mL). The resultant aqueous solution was extracted with ether, basified to pH=12 with 3N NaOH, extracted into ethyl acetate (3×), and the combined organic layers were washed with 100 mL of brine, dried with anhydrous magnesium sulfate and concentrated in vacuo to yield 1.0 g (91%) of the title compound as an oil which was used in next step with out further purification.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. extractionextracted with 3% hydrochloric acid (10 mL)
  4. extractionThe resultant aqueous solution was extracted with ether
  5. extractionextracted into ethyl acetate (3×)
  6. washthe combined organic layers were washed with 100 mL of brine
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ab166b7e5604905ba86a8cac937a9b9
Source dataset
uspto-grants-2006_03
Patent number
US07019019B2

Reaction notes

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