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

HRID 356509ノート

反応式

HRID 356509 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-00b53a1f134344b2a0c9620069791fa5
出典データセット
uspto-grants-1998_11
特許番号
US05834506

反応ノート

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