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

HRID 1003864Notes

Reaction equation

HRID 1003864 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-4866e2dcf32a490ca41a12efdf1dd92a
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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