Sodium hydride → 2-Thiocyanomethyl-3-allyl-4(3H)-quinazolinone

HRID 364624

반응식

HRID 364624 반응식
S[C:2]1[N:11]([CH2:12][CH:13]=[CH2:14])[C:10](=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl[CH2:17][S:18][C:19]#[N:20].[H-].[Na+]>C(COC)OC>[S:18]([CH2:17][C:2]1[N:11]([CH2:12][CH:13]=[CH2:14])[C:10](=[O:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[C:19]#[N:20]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 76755Thiocyanic acid, chloromethyl esterHCID 178456612HCID 178456612, 화합물2회

생성물 1

HCID 202395102-Thiocyanomethyl-3-allyl-4(3H)-quinazolinone

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

To a mixture of 5.8 g (0.03 mole) 2-mercapto-3-allyl-4(3H)-quinazolinone (the product of Example 5) in 200 ml dimethoxyethane, 5.4 g (0.05 mole) chloromethyl thiocyanate and 2.4 g (0.05 mole) 50% sodium hydride were added. The resulting mixture was stirred overnight at ambient temperature, refluxed at 50° C. for 8 hours, stirred overnight, refluxed at 50° C. for 8 hours and stirred overnight. The reaction mixture was washed with water, extracted with methylene chloride, dried over magnesium sulfate and stripped. The oily residue was triturated with ether, to give the above-identified product, as a solid, melting point 73°-76° C.

후처리

  1. temperaturerefluxed at 50° C. for 8 hours
  2. stirringstirred overnight
  3. temperaturerefluxed at 50° C. for 8 hours
  4. stirringstirred overnight
  5. washThe reaction mixture was washed with water
  6. extractionextracted with methylene chloride
  7. dry with materialdried over magnesium sulfate
  8. customThe oily residue was triturated with ether
  9. customto give the above-identified product

출처 및 근거

ORD 기록
ord-1d22afbe27e840f2a92de4ae2e8d78ce
출처 데이터셋
uspto-grants-1986_08
특허 번호
US04605657

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