2-(Trifluoromethyl)phenyl isocyanate → 6-ethoxycarbonyl-5,7-dimethyl-3-[2-(trifluoromethyl)phenyl]-2,4-(1H,3H)-quinazolinedione

HRID 1995644노트

반응식

HRID 1995644 반응식
[F:1][C:2]([F:13])([F:12])[C:3]1[C:4]([N:9]=[C:10]=[O:11])=[CH:5][CH:6]=[CH:7][CH:8]=1.[NH2:14][C:15]1[CH:23]=[C:22]([CH3:24])[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:20]([CH3:30])[C:16]=1[C:17]([OH:19])=O>C(OCC)C>[CH2:28]([O:27][C:25]([C:21]1[C:20]([CH3:30])=[C:16]2[C:15](=[CH:23][C:22]=1[CH3:24])[NH:14][C:10](=[O:11])[N:9]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:2]([F:1])([F:12])[F:13])[C:17]2=[O:19])=[O:26])[CH3:29]

참가 물질

4

반응물 2

HCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 126858402-Amino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid

생성물 1

HCID 155807756-ethoxycarbonyl-5,7-dimethyl-3-[2-(trifluoromethyl)phenyl]-2,4-(1H,3H)-quinazolinedione수율 67.1%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

α,α,α-Trifluoro-o-tolyl isocyanate (434 mg) was added to a solution of 2-amino-5-ethoxycarbonyl-4,6-dimethylbenzoic acid (500 mg) in diethyl ether (22 ml), and the mixture was stirred overnight. The resulting precipitate was filtered off and dissolved in ethanol (15 ml). Then, hydrogen chloride (1 g) was introduced into the solution. The reaction mixture was refluxed for 3 hours and the solvent was evaporated off. The residue was recrystallized from diethyl ether to give 6-ethoxycarbonyl-5,7-dimethyl-3-[2-(trifluoromethyl)phenyl]-2,4-(1H,3H)-quinazolinedione (575 mg, 67%) melting at 175°-176° C. MS: m/e, 406(M+), 377, 361, 357, 337, 332, 314, 309. NMR: δ(ppm, CDCl3) 1.40 (3H, t), 2.30 (3H, s), 2.68 (3H, s), 4.44 (2H, q), 6.70 (1H, b), 7.2-8.0 (4H, m), 10.25 (1H, s).

후처리

  1. filtrationThe resulting precipitate was filtered off
  2. dissolutiondissolved in ethanol (15 ml)
  3. additionThen, hydrogen chloride (1 g) was introduced into the solution
  4. temperatureThe reaction mixture was refluxed for 3 hours
  5. customthe solvent was evaporated off
  6. customThe residue was recrystallized from diethyl ether

출처 및 근거

ORD 기록
ord-e6ad89fef7eb4b849f260bbf02d5ac73
출처 데이터셋
uspto-grants-1983_09
특허 번호
US04405623

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