Triphenylphosphine → HCID 57959820, compound

HRID 1698520Notes

Reaction equation

HRID 1698520 reaction equation
Cl[CH:2]([C:7]1[N:11]([CH3:12])[C:10]([S:13][CH2:14][CH:15]2[CH2:17][CH2:16]2)=[N:9][N:8]=1)[CH2:3][CH:4]1[CH2:6][CH2:5]1.[N-:18]=[N+]=[N-].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.O>[CH:4]1([CH2:3][CH:2]([C:7]2[N:11]([CH3:12])[C:10]([S:13][CH2:14][CH:15]3[CH2:17][CH2:16]3)=[N:9][N:8]=2)[NH2:18])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 57959833HCID 57959833, compound

Product 1

HCID 57959820HCID 57959820, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a crude solution of the 3-(1-chloro-2-cyclopropylethyl)-5-[(cyclopropylmethyl)thio]-4-methyl-4H-1,2,4-triazole from step d in DMF (3 mL) under nitrogen was added sodium azide (1.0 g, 15 mmol). The mixture was stirred at 65° C. for 20 h, then cooled to room temperature, diluted with water and extracted into ethyl acetate. The organic extract was washed with water and then brine before being dried (MgSO4) and concentrated. The residue was taken up in THF (10 mL), and water (2 mL) was added followed by triphenylphosphine (1.6 g, 6.1 mmol). The reaction mixture was stirred under nitrogen for 5 h, then concentrated in vacuo. The residue was dissolved in methanol and applied to an SCX cartridge. Elution with methanol afforded organophosphorus residues and subsequent elution with 2M ammonia in methanol provided the title amine.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted into ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialbrine before being dried (MgSO4)
  6. concentrationconcentrated
  7. additionwater (2 mL) was added
  8. stirringThe reaction mixture was stirred under nitrogen for 5 h
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in methanol
  11. washElution with methanol
  12. customafforded
  13. washorganophosphorus residues and subsequent elution with 2M ammonia in methanol

Sources & evidence

ORD record
ord-0c1d122847104c74b713e554759a519b
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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