Cesium carbonate → Dimethyl-sulfamic acid 5-tert-butyl-2-methyl-4-thiocyanato-phenyl ester

HRID 356509노트

반응식

HRID 356509 반응식
[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:22][N:23]([CH3:28])[S:24](Cl)(=[O:26])=[O:25]>C(#N)C>[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([O:11][S:24](=[O:26])(=[O:25])[N:23]([CH3:28])[CH3:22])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 83372Dimethylsulphamoyl chlorideHCID 105609555-tert-Butyl-2-methyl-4-thiocyanato-phenol

생성물 1

HCID 10496539Dimethyl-sulfamic acid 5-tert-butyl-2-methyl-4-thiocyanato-phenyl ester

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a round bottom flask equipped with a condenser and magnetic stirrer were added 5-tert-butyl-2-methyl-4-thiocyanato-phenol prepared in Example GGG (1.5 g, 6.8 mmol), cesium carbonate (2.44 g, 7.49 mmol), and acetonitrile (30 mL). This slurry was brought to reflux for 15 minutes. Dimethyl sulfamoyl chloride (0.80 mL, 7.49 mmol) was added to the slurry via syringe. The reaction was quenched with brine and extracted with EtOAc; the organic layer was dried (MgSO4) and concentrated. The residue was submitted to column chromatography (7:3 hexane:EtOAc) to give the title compound. 1H NMR (CDCl3) δ 1.46 (s, 9 H), 2.22 (s, 3 H), 3.03 (s, 6 H), 7.30 (s, 1 H), 7.47 (s, 1 H).

후처리

  1. customTo a round bottom flask equipped with a condenser and magnetic stirrer
  2. temperatureto reflux for 15 minutes
  3. customThe reaction was quenched with brine
  4. extractionextracted with EtOAc
  5. dry with materialthe organic layer was dried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-00b53a1f134344b2a0c9620069791fa5
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834506

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