Potassium Carbonate → Tert-Butyl 1,2,6-Thiadiazinane-2-Carboxylate 1,1-Dioxide

HRID 1522056Notes

Reaction equation

HRID 1522056 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][S:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])=[O:7].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[S:6]1(=[O:8])(=[O:7])[NH:5][CH2:4][CH2:3][CH2:2][N:9]1[C:10]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:16]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23584604HCID 23584604, compound

Product 1

HCID 23583903Tert-Butyl 1,2,6-Thiadiazinane-2-Carboxylate 1,1-DioxideYield 40%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of tert-butyl N-(3-chloropropyl)sulfamoylcarbamate (2 g, 7.333 mmol) in DMSO (10 mL), was added K2CO3 (5.068 g, 36.665 mmol) at room temperature. The reaction mixture was agitated for 4 hr and extracted using ethyl acetate and NH4Cl solution. The organic layer was dried over MgSO4. The residue was purified by silica gel column chromatography to give tert-butyl 1,2,6-thiadiazinan-2-carboxylate 1,1-dioxide (689 mg, 2.92 mmol, 40%, white solid). 1H NMR (300 MHz, CDCl3): δ 4.47 (br, 1H), 3.95-3.91 (m, 2H), 3.55-3.49 (m, 2H), 1.89-1.82 (m, 2H), 1.54 (m, 9H).

Workup

  1. extractionextracted
  2. dry with materialThe organic layer was dried over MgSO4
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c4b6b1ef80924fce92eb1f022df06b9f
Source dataset
uspto-grants-2015_07
Patent number
US09073906B2

Reaction notes

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