Triphenylphosphine → HCID 22145389, compound

HRID 1825357Notes

Reaction equation

HRID 1825357 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH2:10][CH2:11]O)[N:5]=1)(=[O:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[SH:32][C:33]1[N:37]([CH3:38])[N:36]=[N:35][N:34]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:1]([C:4]1[CH:8]=[C:7]([CH3:9])[N:6]([CH2:10][CH2:11][S:32][C:33]2[N:37]([CH3:38])[N:36]=[N:35][N:34]=2)[N:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 22145372HCID 22145372, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 22145389HCID 22145389, compoundYield 45.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
5 °C

Procedure

3-Acetyl-5-methyl-1-(2-hydroxyethyl)pyrazole (1.74 g), triphenyl-phosphine (4.071 g) and 5-mercapto-1-methyltetrazole (3.605 g) were dissolved in dry THF (125 ml) and cooled to 5° C. under an atmosphere of argon. A solution of diethylazodicarboxylate (2.70 g) in THF (25 ml) was added dropwise to the stirred, cooled solution. Stirring was continued at 5° C. for 4 h. The reaction mixture was then partitioned between ethyl acetate and water. The organic solution was washed with NaHCO3 solution, brine, dried (MgSO4) and evaporated. Silica gel column chromatography provided the title compound (1.25 g), umax (CH2Cl2) 1683 cm−1; dH (CDCl3) 2.30 (3H, s), 2.55 (3H, s), 3.80 (2H, t), 3.92 (3H, s), 4.59 (2H, t), 6.51 (1H, s); m/z 266.0953 (M+), calculated for C10H14N6OS 266.0950.

Workup

  1. temperaturecooled solution
  2. customThe reaction mixture was then partitioned between ethyl acetate and water
  3. washThe organic solution was washed with NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-2dc3a41dba2e4aaaaebe4eb2ab93cfe6
Source dataset
uspto-grants-2006_05
Patent number
US07045619B2

Reaction notes

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