Sodium Iodide → HCID 15817624, compound

HRID 1886510Notes

Reaction equation

HRID 1886510 reaction equation
[H-].[Na+].Cl[CH2:4][CH2:5][CH2:6][C:7]#[CH:8].[F:9][C:10]([F:15])([F:14])[C:11]([NH2:13])=[O:12].[I-].[Na+].P([O-])(O)(O)=O.[K+]>CN(C)C=O.O>[F:9][C:10]([F:15])([F:14])[C:11]([NH:13][CH2:4][CH2:5][CH2:6][C:7]#[CH:8])=[O:12]

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 24758Sodium hydride2×HCID 67717TrifluoroacetamideHCID 843081-Pentyne, 5-chloro-HCID 516951Monobasic potassium phosphate

Product 1

HCID 15817624HCID 15817624, compoundYield 45.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, Alfa) was rendered oil-free by thoroughly and rapidly washing with pentane and then vacuum-drying. Oil-free sodium hydride (4.40 g, 0.110 mole, 1.1 eq) was added in about 20 portions over 25 min to a solution of 5-chloropentyne (10.6 mL, 0.100 mole, 1.0 eq), trifluoroacetamide (14.13 g, 0.125 mole, 1.25 eq), and sodium iodide (14.99 g, 0.100 mole, 1.0 eq) in dry dimethylformamide (250 mL, Aldrich). The reaction mixture was stirred at 25° for 4.5 h and at 60° for 21 h. After cooling, the reaction mixture was added to a solution of potassium dihydrogen phosphate (43.5 g, 0.250 mole, 2.0 eq) in water (500 mL). This solution was extracted with pentane (2×500 mL) and ether (3×500 mL). The combined organic layers were washed with water (1×100 mL), dried over magnesium sulfate, and concentrated with a rotary evaporator. Fractional distillation twice through a 20 cm Vigreux column afforded 8.09 g (45%) of 5-trifluoroacetamido-1-pentyne (58) as a colorless, mobile liquid (bp 68-69° at 13 torr.)

Workup

  1. washrapidly washing with pentane
  2. customvacuum-drying
  3. temperatureAfter cooling
  4. extractionThis solution was extracted with pentane (2×500 mL) and ether (3×500 mL)
  5. washThe combined organic layers were washed with water (1×100 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated with a rotary evaporator
  8. distillationFractional distillation twice through a 20 cm Vigreux column

Sources & evidence

ORD record
ord-32e31a0cdca9425eb23862ef1420d3c8
Source dataset
uspto-grants-1992_09
Patent number
US05151507

Reaction notes

Loading…