N-Methyl-1,3-propanediamine → 2-Methyl-[1,2,6]thiadiazinane 1,1-dioxide

HRID 1776225Notes

Reaction equation

HRID 1776225 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][NH2:6].[S:7](N)(N)(=[O:9])=[O:8]>N1C=CC=CC=1>[CH3:1][N:2]1[CH2:3][CH2:4][CH2:5][NH:6][S:7]1(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 80511N-Methyl-1,3-propanediamineHCID 82267Sulfamide

Product 1

HCID 100805602-Methyl-[1,2,6]thiadiazinane 1,1-dioxideYield 53.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred mixture of N-methyl-1,3-diaminopropane (1.70 mL, 16.3 mmol) in pyridine (20 mL) was added sulfamide (1.877 g, 19.5 mmol). The mixture was heated in an oil bath at 120° C. for 16 hrs. After cooling to room temperature, the mixture was concentrated and the residue partitioned between ethyl acetate and saturated aqueous sodium chloride. The organic layer was washed with 1N aqueous hydrochloric acid, saturated aqueous sodium chloride, dried (anhydrous sodium sulfate, filtered, and concentrated to afford a colorless oil (1.3 g, 53%). 1H NMR (300 MHz, CDCl3) δ 4.11 (br s, 1H), 3.60-3.48 (m, 2H), 3.32 (t, 2H, J=5.7 Hz), 2.78 (s, 3H), 1.85-1.72 (m, 2H).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated
  3. customthe residue partitioned between ethyl acetate and saturated aqueous sodium chloride
  4. washThe organic layer was washed with 1N aqueous hydrochloric acid, saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4aa9d0c75645435aa30cded2b8a60344
Source dataset
uspto-grants-2016_02
Patent number
US09265772B2

Reaction notes

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