Methanesulfonyl chloride → HCID 86655256, compound

HRID 1890319Notes

Reaction equation

HRID 1890319 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([OH:22])=[N:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][C:18]([F:21])([F:20])[F:19])([O-:3])=[O:2].[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>C(Cl)Cl>[CH3:26][S:23]([O:22][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[C:9]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][C:18]([F:21])([F:19])[F:20])[N:8]=1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178526705HCID 178526705, compound

Product 1

HCID 86655256HCID 86655256, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Nitro-6-(2-(trifluoromethoxy)phenylamino)pyridin-2-ol (1.5 g, 4.8 mmol) was taken up in CH2Cl2 (25 mL). TEA (1.3 ml, 9.5 mmol) was added followed by mesylchloride (0.45 ml, 5.7 mmol). The reaction mixture was stirred at ambient temperature for 1 hour and quenched with 1 N HCl. The layers were separated and the aqueous layer was back extracted with additional CH2Cl2. The combined organic portions were dried over Na2SO4 and concentrated under reduced pressure to give the title compound (1.8 g). 1H NMR (400 MHz, CDCl3) δ ppm 3.26 (s, 3H), 6.54 (d, J=8.8 Hz, 1H), 7.26 (m, 1H), 7.39 (m, 2H), 8.22 (m, 1H), 8.67 (d, J=8.8, 1H), 10.46 (s, 1H).

Workup

  1. customquenched with 1 N HCl
  2. customThe layers were separated
  3. extractionthe aqueous layer was back extracted with additional CH2Cl2
  4. dry with materialThe combined organic portions were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b83a16c15c184239b47a0e8e039e4409
Source dataset
uspto-grants-2013_08
Patent number
US08507473B2

Reaction notes

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