Sodium hydride → HCID 59550877, compound

HRID 1169723Notes

Reaction equation

HRID 1169723 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH3:13])(=[NH:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].[N:16]1([C:22](Cl)=[O:23])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([S:10]([CH3:13])(=[N:12][C:22]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)=[O:23])=[O:11])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 848104-Morpholinecarbonyl chlorideHCID 12463933S-Methyl-S-(4-nitrophenyl)sulfoximine

Product 1

HCID 59550877HCID 59550877, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

100 mg (0.5 mmol) (RS)—S-(4-nitrophenyl)-S-methylsulphoximide in 4 ml dimethylformamide are treated at room temperature with 23.97 mg sodium hydride (55%, 0.55 mmol). The mixture is stirred for 30 minutes at room temperature and for 30 minutes at 50° C. After cooling to room temperature 0.063 ml (0.55 mmol) 4-morpholinylcarbonyl chloride are added. The mixture is stirred for 30 minutes at room temperature and for 2 hours at 50° C. and finally quenched with methanol. After chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate)), 87 mg (0.28 mmol, corresponding to 56% of theor.) of the desired product is obtained.

Workup

  1. additionare added
  2. stirringThe mixture is stirred for 30 minutes at room temperature and for 2 hours at 50° C.
  3. customfinally quenched with methanol
  4. customAfter chromatographic purification (silica gel, hexane/ethyl acetate (0-50% ethyl acetate)), 87 mg (0.28 mmol, corresponding to 56% of theor.) of the desired product
  5. customis obtained

Sources & evidence

ORD record
ord-02b4342f6b064da0af53a1be89e69e69
Source dataset
uspto-grants-2010_11
Patent number
US07825128B2

Reaction notes

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