Triphenylphosphine → HCID 86721895, compound

HRID 1049053Notes

Reaction equation

HRID 1049053 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C1([P:23](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1>[Br-:1].[CH2:13]([NH:12][S:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][PH3+:23])=[CH:4][CH:5]=1)(=[O:11])=[O:10])[CH:14]([CH3:16])[CH3:15]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 65482177HCID 65482177, compound

Product 1

HCID 86721895HCID 86721895, compoundYield 156.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-bromomethyl-N-isobutyl-benzenesulfonamide (1.08 g, 3.53 mmol) and triphenylphosphine (1.39 g, 5.29 mmol) in toluene (20 mL) was heated at reflux for 18 hours. The precipitate was collected from the cooled mixture, washed with toluene and air dried to give 4-isobutylsulfamoyl-benzyl-phosphonium bromide (1.88 g, 94%). 1H NMR (300 MHz, DMSO) δ 7.96-7.88 (m, 2H), 7.79-7.56 (m, 15H), 7.20-7.13 (m, 2H), 5.29 (d, J=16.1 Hz, 2H), 2.53-2.46 (m, 2H), 1.64-1.48 (m, 1H), 0.77 (d, J=6.7 Hz, 6H). LCMS (m/z, Method A) ES+ 488.1 [M+Na]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 hours
  3. customThe precipitate was collected from the cooled mixture
  4. washwashed with toluene and air
  5. customdried

Sources & evidence

ORD record
ord-01d7c21a4ddf417baac379d3f45be5a7
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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