tert-Butanol → HCID 86671521, compound

HRID 538915Notes

Reaction equation

HRID 538915 reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:17])[CH2:6][C:7](=O)[CH2:8][NH:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)[CH3:3].C(O)(C)(C)C.[C:23]([S-:25])#[N:24].[K+]>O>[CH2:2]([O:4][C:5](=[O:17])[CH2:6][C:7]1[NH:24][C:23](=[S:25])[N:9]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:8]=1)[CH3:3]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 516872Potassium thiocyanateHCID 66786996HCID 66786996, compound

Product 1

HCID 86671521HCID 86671521, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 g (0.758 mol) 4-Cyclohexylamino-3-oxo-butyric acid ethyl ester hydrochloride were dissolved in 360 ml water and 120 ml tert-butanol and were heated to 90° C. Then 88.4 g (0.91 mol) KSCN were added and the mixture was heated for 20 s, thereby a phase separation occurred. After cooling to RT, the phases were separated and the aqueous layer was extracted with AcOEt. The combined organic layers were washed with Brine, dried with MgSO4 and concentrated. The solid was digested in MTBE and filtered to yield 192 g (0.715 mol, 94%) of (1-Cyclohexyl-2-thioxo-2,3-dihydro-1H-imidazol-4-yl)-acetic acid ethyl ester as a beige solid. HPLC: tR=1.16 min (YMC J′ sphere ODS H 80 20×2.1 mm, 4 μm, A: H2O+0.05% TFA, B: MeCN, 4%→95% B in 2 min, 1 ml/min, 30° C.); Mass (ES+) (C13H20N2O2S): calculated. 268. found 269 [M+H]+.

Workup

  1. temperaturethe mixture was heated for 20 s
  2. customa phase separation
  3. customthe phases were separated
  4. extractionthe aqueous layer was extracted with AcOEt
  5. washThe combined organic layers were washed with Brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated
  8. filtrationfiltered

Sources & evidence

ORD record
ord-6c64625aa56b40d5adec29e6340f9e29
Source dataset
uspto-grants-2014_10
Patent number
US08865906B2

Reaction notes

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