Dichloromethane → 1-Phenylimidazolidine-2-thione

HRID 1942808Notes

Reaction equation

HRID 1942808 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[S:2].[C:13]1([NH:19][CH2:20][CH2:21][NH2:22])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(Cl)Cl>C1COCC1>[C:13]1([N:19]2[CH2:20][CH2:21][NH:22][C:1]2=[S:2])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 742701,2-Ethanediamine, N1-phenyl-HCID 802641,1'-Thiocarbonyldiimidazole

Product 1

HCID 122691081-Phenylimidazolidine-2-thioneYield 35.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Thiocarbonyldiimidazole (4.51 g, 25.3 mmol) was added to a solution of N-phenylethylenediamine (3 mL, 23.02 mmol) in THF (230 mL) and the mixture was stirred for 2 h at room temperature. DCM was added and the solution was washed with 1N HCl, dried over anhydrous sodium sulfate and concentrated under reduced pressure affording title compound 301 (1.45 g, 8.13 mmol, 35.3% yield). m/z: 179.1 (M+H)+

Workup

  1. washthe solution was washed with 1N HCl
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b383ff0d62bf4bf0992c4ecd6d0fdd00
Source dataset
uspto-grants-2013_03
Patent number
US08389541B2

Reaction notes

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