Potassium Carbonate → tert-Butyl 3-thioureidopropylcarbamate

HRID 2119582Notes

Reaction equation

HRID 2119582 reaction equation
[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH2:11])([CH3:4])([CH3:3])[CH3:2].C([N:21]=[C:22]=[S:23])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.O>[C:1]([O:5][C:6](=[O:12])[NH:7][CH2:8][CH2:9][CH2:10][NH:11][C:22]([NH2:21])=[S:23])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68284Benzoyl isothiocyanateHCID 2735700tert-Butyl (3-aminopropyl)carbamate

Product 1

HCID 20616909tert-Butyl 3-thioureidopropylcarbamateYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2 g (11.47 mmol) (3-Amino-propyl)-carbamic acid tert-butyl ester in 20 ml THF was treated with 1.62 ml (11.47 mmol) Benzoyl isothiocyanate and stirred for 1 h at room temperature. After removal of the volatiles the residue was suspended in 50 ml methanol and 4.8 g (34.4 mmol) K2CO3 in 50 ml water was added. The mixture was stirred at room temperature for 16 h, concentrated, and extracted with ethyl acetate. The combined organic layers were washed with NaHCO3 sat., brine, dried with MgSO4 and evaporated under reduced pressure. The residue was purified by flash column chromatography on silica eluting with ethyl acetate/heptane. The combined product fractions were evaporated under reduced pressure to yield 1.48 g (74%) of the title compound.

Workup

  1. customAfter removal of the volatiles the residue
  2. stirringThe mixture was stirred at room temperature for 16 h
  3. concentrationconcentrated
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with NaHCO3 sat., brine
  6. dry with materialdried with MgSO4
  7. customevaporated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica eluting with ethyl acetate/heptane
  9. customThe combined product fractions were evaporated under reduced pressure

Sources & evidence

ORD record
ord-1ae5e9e3c5ce4fa9aa7c12525f83f810
Source dataset
uspto-grants-2004_02
Patent number
US06686381B2

Reaction notes

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