Triphenylphosphine → [4-(Methanesulfonylaminocarbonyl)butyl]triphenylphosphonium bromide

HRID 2398184Notes

Reaction equation

HRID 2398184 reaction equation
[CH3:1][S:2]([NH:5][C:6](=[O:12])[CH2:7][CH2:8][CH2:9][CH2:10][Br:11])(=[O:4])=[O:3].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(#N)C>[Br-:11].[CH3:1][S:2]([NH:5][C:6]([CH2:7][CH2:8][CH2:9][CH2:10][P+:19]([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:12])(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 202961415-Bromo-N-methanesulfonylpentanamide

Product 1

HCID 19608840[4-(Methanesulfonylaminocarbonyl)butyl]triphenylphosphonium bromideYield 63.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.20 g. (8.57 mmoles) of the N-methanesulfonyl-5-bromovaleramide, prepared as above, 2.24 g. (8.57 mmoles) of triphenylphosphine, and 20 ml. of acetonitrile was heated to reflux under nitrogen overnight. The solution was then concentrated by rotary evaporation and the resultant solid was triturated with hot benzene (4X). The triturated solid was recrystallized from absolute ethanol:ether to afford the white, crystalline [4-(methanesulfonylaminocarbonyl)butyl]triphenylphosphonium bromide weighing 2.80 g. (63.7% yield) melting at 190° -191°.

Workup

  1. temperatureto reflux under nitrogen overnight
  2. concentrationThe solution was then concentrated by rotary evaporation
  3. customthe resultant solid was triturated with hot benzene (4X)
  4. customThe triturated solid was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-f7247f7f73f347e8b7ad0d8201680818
Source dataset
uspto-grants-1977_05
Patent number
US04024179

Reaction notes

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