Cyclopentylamine → N-tert-Butyl-N-cyclopentylthiourea

HRID 396119Notes

Reaction equation

HRID 396119 reaction equation
[C:1]([N:5]=[C:6]=[S:7])([CH3:4])([CH3:3])[CH3:2].[CH:8]1(N)[CH2:12][CH2:11][CH2:10][CH2:9]1.CC[N:16](C(C)C)C(C)C>C(Cl)Cl.CCOC(C)=O>[C:1]([N:5]([CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[C:6]([NH2:16])=[S:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 2906CyclopentylamineHCID 11544tert-Butyl isothiocyanateHCID 81531Diisopropylethylamine

Product 1

HCID 23003023N-tert-Butyl-N-cyclopentylthioureaYield 47%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of t-butyl isothiocyanate (5.0 mL; 39.41 mmol) in CH2Cl2 (200 mL) was added cyclopentylamine (4.67 mL; 47.29 mmol) followed by DIEA and the reaction mixture was stirred at RT for 2 h. The mixture was diluted with EtOAc, washed with 10% citric acid (2×), saturated NaHCO3 (2×), H2O (2×) and brine (1×). The organic layer was dried over anhydrous MgSO4, filtered and evaporated to dryness to obtain the t-butyl-cyclopentylthiourea as a white solid (3.70 g; 47% yield).

Workup

  1. washwashed with 10% citric acid (2×), saturated NaHCO3 (2×), H2O (2×) and brine (1×)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-7f25de4ef1be423dbadde0c400952322
Source dataset
uspto-grants-2003_08
Patent number
US06608027B1

Reaction notes

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