2-Chlorocyclopentanone → 3,4,5,6-Tetrahydro-2H-cyclopenta(d)(1,3)thiazol-2-imine

HRID 589174

Reaction equation

HRID 589174 reaction equation
Cl[CH:2]1[CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:8][C:9]([NH2:11])=[S:10]>O1CCOCC1>[S:10]1[C:3]2[CH2:4][CH2:5][CH2:6][C:2]=2[N:8]=[C:9]1[NH2:11]

Participants

4

Reactant 2

HCID 127512-ChlorocyclopentanoneHCID 2723790Thiourea

Product 1

HCID 3322553,4,5,6-Tetrahydro-2H-cyclopenta(d)(1,3)thiazol-2-imineYield 106.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Chlorocyclopentanone (9.01 g, 74.4 mmol) was added slowly to a 95° C. stirred mixture of thiourea (5.77 g, 75.0 mmol) in 1,4-dioxane (150 mL). After full addition, the temperature was maintained for an hour then the mixture was cooled to room temperature. It was then filtered and washed with 1,4-dioxane and diethyl ether, and dried under air suction to afford 11.15 g white solid. This was partitioned between diethyl ether and saturated aqueous sodium carbonate. The ether layer was washed with brine, dried with Na2SO4, and solvent removed by rotoevaporation to afford 9.8 g beige solid. (Modified procedure from US Patent application 64 699, 2008, Florjancic, A. S.; et al).

Workup

  1. additionAfter full addition
  2. temperaturethe temperature was maintained for an hour
  3. filtrationIt was then filtered
  4. washwashed with 1,4-dioxane and diethyl ether
  5. customdried under air suction

Sources & evidence

ORD record
ord-1928173ea33e40c88666c8de3bd978bb
Source dataset
uspto-grants-2016_01
Patent number
US09227971B2

Linked notes

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