Triethylamine → 2-[2-(Pyridin-4-yl)ethyl]-1lambda~6~,2,6-thiadiazinane-1,1-dione

HRID 1154322Notes

Reaction equation

HRID 1154322 reaction equation
[S:1](Cl)(Cl)(=[O:3])=[O:2].[N:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH2:17][NH2:18])=[CH:8][CH:7]=1.C(N(CC)CC)C>ClCCl>[N:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][CH2:17][NH:18][S:1]2(=[O:3])=[O:2])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 20434879HCID 20434879, compound

Product 1

HCID 204348902-[2-(Pyridin-4-yl)ethyl]-1lambda~6~,2,6-thiadiazinane-1,1-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of sulphuryl chloride (7.5 g) in dichloromethane (20 cm3) was added dropwise over 15 minutes to a stirred solution of N-[2-(4-pyridyl)ethyl]-1,3-diaminopropane (10.0 g) in dichloromethane (100 cm3) and triethylamine (11.2 g) at -20°. The mixture was allowed to warm slowly to room temperature over 1 hour. After stirring for 16 hours the solution was filtered and sodium carbonate solution (50 cm3) was added. The aqueous phase was extracted with methylene chloride (2×50 cm3) and the dried (MgSO4) extracts were evaporated in vacuo to give an oil which was chromatographed on silica ("Merck 60. 9385") eluting with methanol:ethyl acetate, 1:19, to give a solid which was recrystallised from ethanol to afford 2-[2-(4-pyridyl)ethyl] tetrahydro-1,2,6-thiadiazine-1,1-dioxide, m.p. 124°-125° (2.0 g).

Workup

  1. filtrationwas filtered
  2. additionsodium carbonate solution (50 cm3) was added
  3. extractionThe aqueous phase was extracted with methylene chloride (2×50 cm3)
  4. dry with materialthe dried (MgSO4) extracts
  5. customwere evaporated in vacuo
  6. customto give an oil which
  7. customwas chromatographed on silica ("Merck 60. 9385")
  8. washeluting with methanol
  9. customethyl acetate, 1:19, to give a solid which
  10. customwas recrystallised from ethanol

Sources & evidence

ORD record
ord-46d6b08e83f84426b7f71fdf248747b8
Source dataset
uspto-grants-1984_12
Patent number
US04489075

Reaction notes

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