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

HRID 589174

反応式

HRID 589174 の反応式
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]

参加物

4

反応物 2

HCID 127512-ChlorocyclopentanoneHCID 2723790Thiourea

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1928173ea33e40c88666c8de3bd978bb
出典データセット
uspto-grants-2016_01
特許番号
US09227971B2

関連ノート

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