Triethylamine → tert-butyl 4-[N'-(2-fluorophenyl)ureido]-3-methylphenylacetate

HRID 350415Notes

Reaction equation

HRID 350415 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[CH3:16].CCN(CC)CC.[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[N:31]=[C:32]=[O:33]>C1COCC1>[F:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[NH:31][C:32](=[O:33])[NH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])=[CH:4][C:3]=1[CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855882-Fluorophenyl isocyanateHCID 23512173Tert-butyl 4-amino-3-methylphenylacetate

Product 1

HCID 23512195tert-butyl 4-[N'-(2-fluorophenyl)ureido]-3-methylphenylacetateYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl 4-amino-3-methylphenylacetate (1.09 g, 4.93 mmol) and Et3N (755 ml, 5.42 mmol) in THF (10 ml) was added 2-fluorophenyl isocyanate (610 μl, 5.44 mmol) and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated to a small volume and diluted with n-hexane. Resulting precipitate was collected under a reduced pressure and the filtrate was washed with n-hexane to give tert-butyl 4-[N′-(2-fluorophenyl)ureido]-3-methylphenylacetate (1.31 g, 74%) as a white crystalline powder. mp 89–91° C.; 1H-NMR (CDCl3) δ 1.47 (s, 9 H), 2.06 (s, 3 H), 3.49 (s, 2 H), 6.62 (s, 1 H), 6.92–7.09 (m, 5 H), 7.21 (br s, 1 H), 7.49–7.51 (m, 1 H), 8.10–8.15 (m, 1 H); Anal. Calcd for C20H23FN2O3: C, 67.02; H, 6.47; N, 7.82; F, 5.30. Found: C, 66.74; H, 6.35; N, 7.85; F, 5.69.

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. washthe filtrate was washed with n-hexane

Sources & evidence

ORD record
ord-6ee4105d47304d3ebc528da8c2519912
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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