Diethyl Malonate → Diethyl 5-(dimethylamino)-1,3-dithiane-2,2-dicarboxylate

HRID 235676Notes

Reaction equation

HRID 235676 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C1(S([S:21][CH2:22][CH:23]([N:35]([CH3:37])[CH3:36])[CH2:24][S:25]S(C2C=CC=CC=2)(=O)=O)(=O)=O)C=CC=CC=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:10]([O:9][C:1]([C:2]1([C:3]([O:5][CH2:6][CH3:7])=[O:4])[S:25][CH2:24][CH:23]([N:35]([CH3:37])[CH3:36])[CH2:22][S:21]1)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 8471TriethylamineHCID 87176Bensultap

Product 1

HCID 13335399Diethyl 5-(dimethylamino)-1,3-dithiane-2,2-dicarboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 20 ml of chloroform were added 1.6 g (0.01 mole) of diethyl malonate and 4.3 g (0.01 mole) of 1,3-bis(benzenesulfonylthio)-2-(N,N-dimethylamino)propane, and then 2.1 g (0.02 mole) of triethylamine was added thereto at room temperature. After completion of addition, the reaction was allowed to proceed at 40° C. for 4 hours. The reaction mixture was washed with two 20-ml portions of water, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was heated in 20 ml of ether-hexane (1:1) for dissolution and the solution was allowed to stand in the cold overnight. The resulting crystalline precipitate was collected by filtration to give 2.7 g (90%) of 2,2-diethoxycarbonyl-5-(N,N-dimethylamino)-1,3-dithiane as light-yellow crystals melting at 38°-39° C.

Workup

  1. customat room temperature
  2. additionAfter completion of addition
  3. washThe reaction mixture was washed with two 20-ml portions of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. temperatureThe residue was heated in 20 ml of ether-hexane (1:1) for dissolution
  7. customto stand in the cold overnight
  8. filtrationThe resulting crystalline precipitate was collected by filtration

Sources & evidence

ORD record
ord-91e24f3ca80e410385b4f244b3358ebb
Source dataset
uspto-grants-1987_02
Patent number
US04640929

Reaction notes

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