Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate → HCID 59731060, compound

HRID 130626Notes

Reaction equation

HRID 130626 reaction equation
[F:1][S:2]([F:17])([F:16])([F:15])([F:14])[C:3]1[CH:4]=[C:5]([NH:9]S(C)(=O)=O)[CH:6]=[CH:7][CH:8]=1.F[C:19]1[C:28]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([CH3:33])[CH:20]=1>CN1C(=O)CCC1.CC(=O)OCC>[CH3:32][S:29]([C:28]1[C:19]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([S:2]([F:1])([F:14])([F:15])([F:16])[F:17])[CH:4]=2)=[CH:20][C:21]([CH3:33])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:30])=[O:31]

Participants

5

Reactant 2

HCID 10538364Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoateHCID 59731058Sulfur, pentafluoro[3-[(methylsulfonyl)amino]phenyl]-, (OC-6-21)-

Product 1

HCID 59731060HCID 59731060, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

1.0 g of N-(3-pentafluorosulfanylphenyl)methanesulfonamide, 0.8 g of methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate and 1.4 ml of TBTMG were dissolved in 10 ml of NMP (anhydrous) and stirred at 150° C. for 7 h. The mixture was then diluted with 100 ml of EA and washed firstly 3 times with 30 ml of a saturated aqueous Na2CO3 solution each time and then 3 times with 30 ml of a saturated aqueous NaHSO4 solution each time. The residue after drying over MgSO4 and removal of the solvent in vacuo was chromatographed on silica gel with DIP. 370 mg of a resinous solid were obtained.

Workup

  1. washwashed firstly 3 times with 30 ml of a saturated aqueous Na2CO3 solution each time
  2. dry with materialThe residue after drying over MgSO4 and removal of the solvent in vacuo
  3. customwas chromatographed on silica gel with DIP

Sources & evidence

ORD record
ord-106cd67a15d34a0d9decf12da6cd1682
Source dataset
uspto-grants-2008_06
Patent number
US07381841B2

Reaction notes

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