Methyl 4-fluoro-5-methanesulfonyl-2-methylbenzoate → Methyl 5-methanesulfonyl-2-methyl-4-(3-pentafluorosulfanylphenyl-amino)benzoate

HRID 130626ノート

反応式

HRID 130626 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 59731060Methyl 5-methanesulfonyl-2-methyl-4-(3-pentafluorosulfanylphenyl-amino)benzoate収率 25.6%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-106cd67a15d34a0d9decf12da6cd1682
出典データセット
uspto-grants-2008_06
特許番号
US07381841B2

反応ノート

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