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

HRID 1995644Notes

Reaction equation

HRID 1995644 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-e6ad89fef7eb4b849f260bbf02d5ac73
Source dataset
uspto-grants-1983_09
Patent number
US04405623

Reaction notes

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