N-Methyl-N-vinylacetamide → N-[2-(Diphenylphosphanyl)ethyl]-N-methylacetamide

HRID 638407Notes

Reaction equation

HRID 638407 reaction equation
[CH:1]([N:3]([CH3:7])[C:4](=[O:6])[CH3:5])=[CH2:2].[C:8]1([PH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>>[CH3:7][N:3]([CH2:1][CH2:2][P:14]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4](=[O:6])[CH3:5]

Participants

3

Reactant 2

HCID 18530N-Methyl-N-vinylacetamideHCID 70017Diphenylphosphine

Product 1

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

Conditions

Temperature
100 °C

Procedure

A 100 ml 3-necked round bottomed flash was heated to 100° C. under a nitrogen atmosohere and 7.14 g diohenylphosphine (38.4 mmole), 0.15 g 2,2'-azobis (2-methyloropionitrile), 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 disolayed 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-2f3a950c6550402981bca964f059c3ed
Source dataset
uspto-grants-1985_12
Patent number
US04560806

Reaction notes

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