Sodium hydride → 4-[2,3-Bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-propyl]-morpholine

HRID 1358767Notes

Reaction equation

HRID 1358767 reaction equation
[N:1]1([CH2:7][CH:8]([OH:11])[CH2:9][OH:10])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:15]1[CH:20]=[CH:19][C:18]([S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])=[CH:17][C:16]=1[N+:28]([O-:30])=[O:29]>C(#N)C>[N+:28]([C:16]1[CH:17]=[C:18]([S:21]([C:24]([F:27])([F:26])[F:25])(=[O:23])=[O:22])[CH:19]=[CH:20][C:15]=1[O:11][CH:8]([CH2:9][O:10][C:15]1[CH:20]=[CH:19][C:18]([S:21]([C:24]([F:26])([F:27])[F:25])(=[O:23])=[O:22])=[CH:17][C:16]=1[N+:28]([O-:30])=[O:29])[CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)([O-:30])=[O:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1108503-Morpholinopropane-1,2-diolHCID 15479561-Chloro-2-nitro-4-trifluoromethanesulfonylbenzene

Product 1

HCID 181853224-[2,3-Bis-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-propyl]-morpholine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using the same procedure as for Example 54, a mixture of 3-morpholin-4-yl-propane-1,2-diol (40 mg, 0.25 mmol), sodium hydride (60%, 30 mg) and 1-chloro-2-nitro-4-trifluoromethanesulfonyl-benzene (174 mg, 0.6 mmol) in acetonitrile (1 mL) was heated to reflux, worked-up and purified on silica gel to give the title compound. 1H NMR (360 MHz, DMSO-d6) δ 8.59 (d, J=2.3 Hz, 2H), 8.35 (dd, J=2.3 & 9.2 Hz, 1H), 8.30 (dd, J=2.3 & 9.2 Hz, 1H), 7.97 (d, J=9.2 Hz, 1H), 7.79 (d, J=9.2 Hz, 1H), 5.49 (m, 1H), 4.79 (m, 1H), 4.66 (m, 1H), 3.41 (m, 4H), 2.74 (d, J=6.1 Hz, 2H), 2.4-2.5 (m, 4H). MS+ve APCI 668 [M+1].

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. custompurified on silica gel

Sources & evidence

ORD record
ord-260d7c1c55314ffdbbde275073ad58bb
Source dataset
uspto-grants-2003_07
Patent number
US06596772B1

Reaction notes

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