Methanesulfonyl chloride → N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamide

HRID 2044099Notes

Reaction equation

HRID 2044099 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[C:16]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[O:17]>N1C=CC=CC=1>[N:18]1([C:16]([C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=2[NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[O:17])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 60181686(2-Amino-4-nitrophenyl)(morpholin-4-yl)methanone

Product 1

HCID 66833433N-(2-(Morpholine-4-carbonyl)-5-nitrophenyl)methanesulfonamideYield 14.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (0.179 mL, 2.302 mmol) was added to a solution of (2-amino-4-nitrophenyl)(morpholino)methanone (0.5783 g, 2.302 mmol) in pyridine (3 mL) at 0° C. After 30 min at 0° C., the pyridine solvent was evaporated under reduced pressure. The resulting brown oil was triturated with hot CH2Cl2 and filtered. The filtrate was concentrated and purified by silica gel chromatography, eluting with 30-100% EtOAc in hexanes, to give the expected product as yellow solid (108 mg, 14% yield). LCMS: (M+H)+=330.0. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.83 (1H, s), 8.24 (1H, d, J=2.26 Hz), 8.07 (1H, dd, J=8.41, 1.88 Hz), 7.61 (1 H, d, J=8.53 Hz), 3.69 (2H, d, J=4.02 Hz), 3.61 (2H, br. s.), 3.57 (2H, d, J=4.27 Hz), 3.16-3.22 (2H, m), 3.10 (3H, s).

Workup

  1. customthe pyridine solvent was evaporated under reduced pressure
  2. customThe resulting brown oil was triturated with hot CH2Cl2
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography
  6. washeluting with 30-100% EtOAc in hexanes

Sources & evidence

ORD record
ord-c0fe81b619874200aa934a5a47c5ead1
Source dataset
uspto-grants-2013_11
Patent number
US08586751B2

Reaction notes

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