Isopropylamine → N-tert-Butyl-N'-propan-2-ylthiourea

HRID 2242446Notes

Reaction equation

HRID 2242446 reaction equation
[C:1]([N:5]=[C:6]=[S:7])([CH3:4])([CH3:3])[CH3:2].[CH:8]([NH2:11])([CH3:10])[CH3:9].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCOC(C)=O>[C:1]([NH:5][C:6]([NH:11][CH:8]([CH3:10])[CH3:9])=[S:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 11544tert-Butyl isothiocyanateHCID 81531Diisopropylethylamine

Product 1

HCID 12750667N-tert-Butyl-N'-propan-2-ylthioureaYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butylisothiocyanate (5.0 mL, 39 mmol) in CH2Cl2 (200 mL) were added isopropylamine (4.0 mL, 47 mmol) and diisopropylethylamine (DIEA) (6.8 mL, 39 mmol), and the mixture was stirred at rt for 2 h. The reaction mixture was diluted with EtOAc, washed with 10% citric acid (2×), saturated NaHCO3 (2×), H2O (2×), and brine (1×). The organic layer was dried (MgSO4) and evaporated to yield the title compound (3.3 g, 52%) as a white solid which was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-cc759b12af6f4de4a49133f56657847a
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

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