Triethylamine → 2-Methylsulfonylamino-4-morpholin-4-yl-benzoic acid

HRID 349701

反応式

HRID 349701 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CN([Si](C)(C)C)C(=O)C(F)(F)F.[CH3:29][S:30](Cl)(=[O:32])=[O:31].C(N(CC)CC)C>C(Cl)Cl>[CH3:29][S:30]([NH:1][C:2]1[CH:10]=[C:9]([N:11]2[CH2:12][CH2:13][O:14][CH2:15][CH2:16]2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])(=[O:32])=[O:31]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 32510N-methyl-N-(trimethylsilyl)trifluoroacetamideHCID 178082042-Amino-4-(morpholin-4-yl)benzoic acid

生成物 1

HCID 588052022-Methylsulfonylamino-4-morpholin-4-yl-benzoic acid

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a suspension of 2-amino-4-morpholin-4-yl-benzoic acid (230 mg; 1.04 mmol) in CH2Cl2 (3 mL) was added N-methyl-N-(trimethylsilyl)trifluoroacetamide (0.4 mL; 2.1 mmol) via syringe at room temperature under a nitrogen atmosphere. The resulting mixture was heated to reflux for 10 minutes, then allowed to cool to room temperature. Methanesulfonyl chloride (1.2 eq.) and triethylamine (1.2 eq.) were added, and the resulting mixture allowed to stir for 2 hours. The reaction was diluted with CH2Cl2 (30 mL) and washed with water (2×10 mL) and brine, then dried (MgSO4), filtered, and concentrated in vacuo to provide the sulfonamide as a white solid (280 mg; 90%).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 10 minutes
  3. washwashed with water (2×10 mL) and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-eba7adbb842e452f8b50fd0f0a59d6b7
出典データセット
uspto-grants-2007_02
特許番号
US07179912B2

関連ノート

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