Diethyl Ether → 2-Sulfanylidene-1,3-thiazolidine-3-carbonyl chloride

HRID 236283

Reaction equation

HRID 236283 reaction equation
[SH:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1.CCN(CC)CC.[C:14](Cl)([Cl:16])=[O:15].CCOCC>C1COCC1.C1(C)C=CC=CC=1>[S:1]=[C:2]1[N:6]([C:14]([Cl:16])=[O:15])[CH2:5][CH2:4][S:3]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6371PhosgeneHCID 8471TriethylamineHCID 178527880HCID 178527880, compound

Product 1

HCID 235066662-Sulfanylidene-1,3-thiazolidine-3-carbonyl chlorideYield 65,531.898%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 2-mercaptothiazoline (2.0 g, 0.0168 mmol) and Et3N (2.9 ml, 0.021 mol) in THF (30 ml) was added dropwise to a solution of phosgene (2.37 g, 0.0239 mol) in toluene (12 ml) at 5° C. for 7 min. The mixture was stirred at 5° C. for 5 min and then filtered to remove the precipitate. The filtrate was evaporated in vacuo to give a crystalline residue. To the residue was added ether (10 ml) and the ether was evaporated in vacuo. This operation was repeated twice. 2-Thioxo-3-thiazolidinecarbonyl chloride (2,0 g) was obtained as a solid. 65.5% yield. IR (Nujol).

Workup

  1. filtrationfiltered
  2. customto remove the precipitate
  3. customThe filtrate was evaporated in vacuo
  4. customto give a crystalline residue
  5. customthe ether was evaporated in vacuo

Sources & evidence

ORD record
ord-38183b71ef304e3ba36e202eb35f3851
Source dataset
uspto-grants-1987_02
Patent number
US04643991

Linked notes

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