Thionyl Chloride → 5-[(2-Ethoxycarbonylethyl)thio]-4-[(2-ethoxycarbonylethyl)thiomethyl]-1,2,3-thiadiazole

HRID 1108429Notes

Reaction equation

HRID 1108429 reaction equation
C(OC([NH:6][N:7]=[C:8]([CH2:18][S:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:9][S:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)C.[S:27](Cl)(Cl)=O>ClCCCl>[CH2:16]([O:15][C:13]([CH2:12][CH2:11][S:10][C:9]1[S:27][N:6]=[N:7][C:8]=1[CH2:18][S:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[O:14])[CH3:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 158852841,3-Bis[(2-ethoxycarbonylethyl)thio]acetone ethoxycarbonylhydrazone

Product 1

HCID 158852855-[(2-Ethoxycarbonylethyl)thio]-4-[(2-ethoxycarbonylethyl)thiomethyl]-1,2,3-thiadiazoleYield 100.9%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of the hydrazone (7.2 g, 17.6 mmol) in 1,2-dichloroethane (20 mL) was added thionyl chloride (3.9 mL, 53 mmol) at 0° C. and stirred overnight at room temperature. The mixture was concentrated to a volume of 10 mL, diluted with dichloromethane, washed with aqueous sodium bicarbonate, dried over sodium sulfate, and then concentrated to dryness, affording 6.47 g of 5-[(2-ethoxycarbonylethyl)thio]-4-[(2-ethoxycarbonylethyl)thiomethyl]-1,2,3-thiadiazole. 1H NMR (CDCl3) δ 1.2-1.3 (m, 6H), 2.60 (t, 2H, J=7), 2.68 (t, 2H, J=7), 2.77 (t, 2H, J=7), 3.24 (t, 2H, J=7), 4.07 (s, 2H), 4.1-4.2 (m, 4H).

Workup

  1. concentrationThe mixture was concentrated to a volume of 10 mL
  2. additiondiluted with dichloromethane
  3. washwashed with aqueous sodium bicarbonate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-d53b59e4b0fc4f8faa6eb3d1f0cce167
Source dataset
uspto-grants-2000_05
Patent number
US06066630

Reaction notes

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