Ammonia → Tert-butyl 3-sulfamoylbenzoate

HRID 132069

反応式

HRID 132069 の反応式
S(=O)(=O)(O)O.[O-]S([O-])(=O)=O.[Mg+2].Cl[S:13]([C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19]([OH:21])=[O:20])(=[O:15])=[O:14].[CH3:25][C:26](O)([CH3:28])[CH3:27].[NH3:30]>C(Cl)Cl.CO>[C:26]([O:21][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][CH:24]=[C:16]([S:13](=[O:15])(=[O:14])[NH2:30])[CH:17]=1)([CH3:28])([CH3:27])[CH3:25]

参加物

8

反応物 5

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 77641Benzoic acid, 3-(chlorosulfonyl)-

生成物 1

HCID 59733695Tert-butyl 3-sulfamoylbenzoate収率 42.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

Sulfuric acid (conc., 498 μL, 9.06 mmol) was added to a suspension of MgSO4 (4.36 g, 36.22 mmol) in CH2Cl2 (36 mL). The reaction mixture was stirred for 15 minutes, treated with 3-chlorosulfonyl-benzoic acid (Aldrich, 2 g, 9.06 mmol) and 2-methyl-propan-2-ol (anhydrous, 4.33 mL, 45.27 mmol), capped tightly, and stirred overnight at room temperature. The next day, the mixture was cooled to 0° C., treated with 7N NH3 in methanol (Aldrich, 40 mL) dropwise, and stirred for 30 minutes. The solvents were removed in vacuo and the crude was dissolved in ethyl acetate and saturated NaHCO3. The organic layer was washed with saturated NaHCO3, water, and brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as a white solid (1 g, 42.9% yield). 1H-NMR (CDCl3): δ 8.51-8.53 (m, 1H), 8.20-8.21 (m, 1H), 8.08-8.11 (m, 1H), 7.57-7.62 (m, 1H), 5.09 (bs, 2H), and 1.61 (s, 9H).

後処理

  1. customcapped tightly
  2. stirringstirred overnight at room temperature
  3. stirringstirred for 30 minutes
  4. customThe solvents were removed in vacuo
  5. dissolutionthe crude was dissolved in ethyl acetate
  6. washThe organic layer was washed with saturated NaHCO3, water, and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-14e21cc56839443387ef6672069b44f4
出典データセット
uspto-grants-2008_06
特許番号
US07385066B2

関連ノート

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