Benzoyl isothiocyanate → (3-(2-Oxo-1-pyrrolidinyl)propyl)thiourea

HRID 2218509

Reaction equation

HRID 2218509 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][C:6]1=[O:10].C([N:19]=[C:20]=[S:21])(=O)C1C=CC=CC=1>C(Cl)(Cl)Cl>[O:10]=[C:6]1[CH2:7][CH2:8][CH2:9][N:5]1[CH2:4][CH2:3][CH2:2][NH:1][C:20]([NH2:19])=[S:21]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 821111-(3-Aminopropyl)-2-pyrrolidinone

Product 1

HCID 85990655(3-(2-Oxo-1-pyrrolidinyl)propyl)thioureaYield 79.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-(3-aminopropyl)-2-pyrrolidinone (560 μL, 4 mmol) and benzoyl isothiocyanate (536 μL, 4 mmol) was dissolved in chloroform (3 mL), stirred at room temperature for 30 min, then concentrated in vacuo. The resulting residue was dissolved in concentrated HCl (3 mL), heated at 95° C. for 2 h, then concentrated in vacuo. The resulting residue was dissolved in water and washed with dichloromethane (2×30 mL), then basified with 2 M NaOH and extracted with dichloromethane (2×30 mL). The combined extracts were dried over MgSO4 and concentrated to provide 1-(3-(2-oxopyrrolidin-1-yl)propyl)thiourea (638 mg) as a pale yellow oil.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in concentrated HCl (3 mL)
  3. temperatureheated at 95° C. for 2 h
  4. concentrationconcentrated in vacuo
  5. dissolutionThe resulting residue was dissolved in water
  6. washwashed with dichloromethane (2×30 mL)
  7. extractionextracted with dichloromethane (2×30 mL)
  8. dry with materialThe combined extracts were dried over MgSO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3e619942f6c84be883807614ffa21f18
Source dataset
uspto-grants-2008_08
Patent number
US07410988B2

Linked notes

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