Water → 3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate

HRID 1188259Notes

Reaction equation

HRID 1188259 reaction equation
[F:1][C:2]([F:26])([F:25])[S:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:24])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)=[CH:13][O:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4].[CH3:27][S:28](Cl)(=[O:30])=[O:29].O>N1C=CC=CC=1>[F:26][C:2]([F:1])([F:25])[S:3]([O:6][C:7]1[CH:16]=[C:15]2[C:10]([C:11](=[O:24])[C:12]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:28]([CH3:27])(=[O:30])=[O:29])=[CH:19][CH:18]=3)=[CH:13][O:14]2)=[CH:9][CH:8]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 866950533-(4-aminophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate

Product 1

HCID 866950543-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonateYield 75.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 3-(4-aminophenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate (2.2 g, 7.12 mmol) in pyridine (10 mL) at 0° C. was added methanesulfonyl chloride (1.1 mL, 14.24 mmol) over 5 minutes, and then warmed up to room temperature under stirring conditions. After 2 hours the reaction was complete, and water was added in portions under vigorous stirring. The organic phase was then separated and concentrated and the resulting solids were filtered and dried under high vacuum. The solids were heated in acetonitrile, stirred until room temperature was achieved, then filtered off to give 3-(4-(methylsulfonamido)phenyl)-4-oxo-4H-chromen-7-yl trifluoromethanesulfonate (2.49 g). 1H NMR (DMSO, 400 MHz) δ 9.87 (s, 1H); 8.60 (s, 1H); 8.31 (d, J=8.0 Hz, 1H); 8.09 (s, 1H); 7.65 (d, J=8.0 Hz, 1H); 7.57 (d, J=8.4 Hz, 2H); 7.27 (d, J=8.4 Hz, 2H); 3.01 (s, 3 H).

Workup

  1. customThe organic phase was then separated
  2. concentrationconcentrated
  3. filtrationthe resulting solids were filtered
  4. customdried under high vacuum
  5. temperatureThe solids were heated in acetonitrile
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-75a08bd057c14a8cbbb22db506baacef
Source dataset
uspto-grants-2014_03
Patent number
US08673966B2

Reaction notes

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