Ammonia → Tert-butyl 3-sulfamoylbenzoate

HRID 252218

반응식

HRID 252218 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

HCID 59733695Tert-butyl 3-sulfamoylbenzoate수율 42.9%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5cf8e981a9a04de19c96d38c95f3a4b8
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868023B2

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