Methyl iodide → Methyl 3-(4-tert-butyl-n-methylphenylsulfonamido)thiophene-2-carboxylate

HRID 1925705

反応式

HRID 1925705 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22][CH3:23])=[O:21])(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:24](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.Cl>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([N:14]([C:15]2[CH:19]=[CH:18][S:17][C:16]=2[C:20]([O:22][CH3:23])=[O:21])[CH3:24])(=[O:12])=[O:13])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 8015643Methyl 3-(4-tert-butylphenylsulfonamido)thiophene-2-carboxylate

生成物 1

HCID 59180428Methyl 3-(4-tert-butyl-n-methylphenylsulfonamido)thiophene-2-carboxylate収率 83.6%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

To a solution of 55 (0.15 g; 0.42 mmol) in N,N-dimethylformamide (2 mL) at room temperature was added potassium carbonate (0.282 g; 2.12 mmol) followed by iodomethane (0.053 mL; 0.85 mmol). The reaction mixture was heated at 65° C. for 12 hours, cooled to room temperature, diluted with aqueous hydrochloric acid (50 mL; 2M) and extracted with dichloromethane (3×25 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure to yield a crude residue that was purified by chromatography on silica gel eluting with a 0 to 10% ethyl acetate/hexanes gradient to give the title product (0.129 g).

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with dichloromethane (3×25 mL)
  3. dry with materialThe combined organic extracts were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto yield a crude residue that
  7. customwas purified by chromatography on silica gel eluting with a 0 to 10% ethyl acetate/hexanes gradient

出典と根拠

ORDレコード
ord-111159a13811473b8c548de7de1a6a4a
出典データセット
uspto-grants-2012_05
特許番号
US08178699B2

関連ノート

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