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

HRID 1995644ノート

反応式

HRID 1995644 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e6ad89fef7eb4b849f260bbf02d5ac73
出典データセット
uspto-grants-1983_09
特許番号
US04405623

反応ノート

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