Azobisisobutyronitrile → N-[2-(Diphenylphosphanyl)ethyl]-N-methylacetamide

HRID 365219Notes

Reaction equation

HRID 365219 reaction equation
[C:1]1([PH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH:26]([N:28]([CH3:32])[C:29](=[O:31])[CH3:30])=[CH2:27]>>[CH3:32][N:28]([CH2:26][CH2:27][P:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:29](=[O:31])[CH3:30]

Participants

4

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 18530N-Methyl-N-vinylacetamideHCID 70017Diphenylphosphine2×

Product 1

HCID 53656792N-[2-(Diphenylphosphanyl)ethyl]-N-methylacetamideYield 94%

Conditions

Temperature
100 °C

Procedure

A 100 ml 3-necked round bottomed flask was heated to 100° C. under a nitrogen atmosphere and 7.14 g diphenyl-phosphine (38.4 mmole), 0.15 g 2,2'-azobis (2-methylpropionitrile), and 3.77 g N-vinyl-N-methyl acetamide (38.1 mmole) from Polysciences were added in the stated sequence. The reaction was maintained at 100° C. for 45 minutes under a nitrogen atmosphere and then evacuated (1 mm) for 24 hours at 100° C. A viscuous oil resulted whose infrared spectrum displayed a strong γ (CO) band at 1645 cm-1 and a small γ (P-H) band at 2300 cm-1 due to a small amount of diphenylphosphine impurity. The elemental analysis was the following: calculated (found); C, 71.58 (69.89); H, 7.02 (7.15); N, 4.91 (4.57); P, 10.87 (10.97). The yield was 94%.

Workup

  1. temperatureThe reaction was maintained at 100° C. for 45 minutes under a nitrogen atmosphere
  2. customevacuated (1 mm) for 24 hours at 100° C
  3. customA viscuous oil resulted whose infrared spectrum

Sources & evidence

ORD record
ord-04605404af5b4812b2bb23ce2b3237c5
Source dataset
uspto-grants-1986_08
Patent number
US04608444

Reaction notes

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