1,3-Propanedithiol → [5-(Trifluoromethyl)-1,2-oxazol-3-yl]methanamine

HRID 1025975Notes

Reaction equation

HRID 1025975 reaction equation
[N:1]([CH2:4][C:5]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[O:7][N:6]=1)=[N+]=[N-].C(N(CC)CC)C.C(S)CCS.[H-].[Na+]>CC(O)C>[F:13][C:10]([F:11])([F:12])[C:8]1[O:7][N:6]=[C:5]([CH2:4][NH2:1])[CH:9]=1

Participants

6

Reactant 4

HCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 24758Sodium hydrideHCID 866631403-(Azidomethyl)-5-(trifluoromethyl)isoxazole

Product 1

HCID 66678829[5-(Trifluoromethyl)-1,2-oxazol-3-yl]methanamineYield 62.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 6.26 g 3-(azidomethyl)-5-(trifluoromethyl)isoxazole in 100 mL 2-propanol were added 9.08 mL triethyl amine and 330 uL 1,3-propanedithiol. 2.45 g sodiumhydride were added portion wise and stirred at RT for 16 h. The reaction mixture was concentrated in vacuo. The residue was poured carefully into 180 mL 10% acetic acid and washed with diethyl ether/heptane mixture 1.1 (3×50 mL) The aqueous layer was basified with conc. NaOH to pH=12 (50 mL), saturated with NaCl and extracted with CH2Cl2 (3×250 mL). The combined organic layer was dried over Na2SO4, filtered off and concentrated in vacuo to yield 3.4 g of the title compound as yellow oil; LC-MS (UV peak area/ESI) 97.6%, 167.043 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe residue was poured carefully into 180 mL 10% acetic acid
  3. washwashed with diethyl ether/heptane mixture 1.1 (3×50 mL) The aqueous layer
  4. extractionextracted with CH2Cl2 (3×250 mL)
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. filtrationfiltered off
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9b9a7d1a21db4dbb826aa16d382affb7
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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