Cyanomethylenetributylphosphorane → 4-(4-(2-Nitrobenzenesulfonyl)morpholin-2-yl)phenyl 2-nitrobenzenesulfonate

HRID 253010Notes

Reaction equation

HRID 253010 reaction equation
C(C=P(CCCC)(CCCC)CCCC)#N.[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36](O)[CH2:37][N:38]([CH2:51][CH2:52][OH:53])[S:39]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[N+:48]([O-:50])=[O:49])(=[O:41])=[O:40])=[CH:32][CH:31]=1)(=[O:28])=[O:27])([O-:19])=[O:18]>C1(C)C=CC=CC=1>[N+:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([O:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]2[O:53][CH2:52][CH2:51][N:38]([S:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=3[N+:48]([O-:50])=[O:49])(=[O:40])=[O:41])[CH2:37]2)=[CH:32][CH:31]=1)(=[O:27])=[O:28])([O-:19])=[O:18]

Participants

4

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 866312124-(1-Hydroxy-2-(N-(2-hydroxyethyl)-2-nitrophenylsulfonamido)ethyl)phenyl 2-nitrobenzenesulfonate

Product 1

HCID 866312134-(4-(2-Nitrobenzenesulfonyl)morpholin-2-yl)phenyl 2-nitrobenzenesulfonateYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 1 M toluene solution of 5.87 ml (5.87 mmol) of (cyanomethylene)tributylphosphorane was added to a solution of 2.22 g (3.91 mmol) of the title compound produced in step (ii) of Reference Example 12 in toluene (55.0 ml), and the mixture was stirred with heating under reflux for 1 hr 20 min. The reaction solution was then cooled to room temperature, and the solvent was removed under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give 1.16 g (yield 54%) of the title compound.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr 20 min
  3. customthe solvent was removed under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-5f62198bd3354a0a933cb06db3cebddb
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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