Triethylamine → tertbutyl 3-methoxy-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetate

HRID 354356Notes

Reaction equation

HRID 354356 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[O:16][CH3:17].CCN(CC)CC.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[N:33]=[C:34]=[O:35]>C1COCC1>[CH3:17][O:16][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:34]([NH:33][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:26]([F:25])([F:36])[F:37])=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 167942-(Trifluoromethyl)phenyl isocyanateHCID 22244730HCID 22244730, compound

Product 1

HCID 23512196tertbutyl 3-methoxy-4-[N'-(2-trifluoromethylphenyl)ureido]phenylacetateYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-amino-3-methoxyphenylacetate (1.11 g, 4.68 mmol) and Et3N (720 ml 5.17 mmol) in THF (10 ml) was added 2-trifluoromethylphenyl isocyanate (707 ml, 4.68 mmol) and the reaction mixture was stirred at room temperature for 2 days. The reaction mixture was concentrated to a small volume and diluted with n-hexane. Resulting precipitate was collected under a reduced pressure and washed with n-hexane to give tert-butyl 3-methoxy-4-[N′-(2-trifluoromethylphenyl)ureido]phenylacetate (1.11 g, 56%) as a white crystalline powder. mp 131-133° C.; 1H-NM (CDCl3) δ1.44 (s, 9 H), 3.49 (s, 2 H), 3.85 (s, 3 H), 6.83-6.88 (m, 3 H), 6.98 (br s, 1 H), 7.17-7.21 (m, 1 H), 7.52-7.59 (m, 2 H), 7.89-7.91 (m, 1 H), 8.04-8.06 (m, 1 H).

Workup

  1. concentrationThe reaction mixture was concentrated to a small volume
  2. additiondiluted with n-hexane
  3. customResulting precipitate
  4. customwas collected under a reduced pressure
  5. washwashed with n-hexane

Sources & evidence

ORD record
ord-7be97d886a424b05a2557413b5d03127
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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