Allyl Isothiocyanate → 3-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

HRID 1886896노트

반응식

HRID 1886896 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][C:4]2([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:3]=1[C:17]([O:19]CC)=O.[CH2:22]([N:25]=[C:26]=[S:27])[CH:23]=[CH2:24].[OH-].[K+]>C(O)C.O>[CH2:22]([N:25]1[C:17](=[O:19])[C:3]2[C:4]3([CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=3[C:2]=2[NH:1][C:26]1=[S:27])[CH:23]=[CH2:24]

참가 물질

6

반응물 3

HCID 5971Allyl IsothiocyanateHCID 14797Potassium HydroxideHCID 793326ethyl 1-aminospiro[4H-naphthalene-3,1'-cyclohexane]-2-carboxylate

생성물 1

HCID 7188153-allyl-2-thioxo-2,3-dihydro-1H-spiro[benzo[h]quinazoline-5,1'-cyclohexan]-4(6H)-one

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
85 °C

실험 절차

Ethyl 4′-amino-1′H-spiro[cyclohexane-1,2′-naphthalene]-3′-carboxylate 18 (Scheme 8, 1.66 g, 5.82 mmol) and allyl isothiocyanate (0.600 ml, 6.13 mmol) were dissolved in Ethanol (9.69 ml) and refluxed at 85° C. for 10 h. A solution of potassium hydroxide (0.653 g, 11.63 mmol) in Water (9.69 ml) was then added and the reaction mixture was refluxed for 3 h. The cooled r×n mixture was acidified to pH 3.0-3.5. The precipitate was filtered off, washed with water and recrystallized from butanol.

후처리

  1. temperaturethe reaction mixture was refluxed for 3 h
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customrecrystallized from butanol

출처 및 근거

ORD 기록
ord-0a5105e7c60c425fa46e70fce73a0828
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501722B2

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