2-Bromophenyl isocyanate → tert-butyl 4-[N'-(2-bromophenyl)ureido]-3-methylphenylacetate

HRID 350424Notes

Reaction equation

HRID 350424 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].[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]=[C:25]=[O:26]>C1COCC1>[Br:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[NH:24][C:25](=[O:26])[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

4

Reactant 2

HCID 1370972-Bromophenyl isocyanateHCID 23512173Tert-butyl 4-amino-3-methylphenylacetate

Product 1

HCID 23512004tert-butyl 4-[N'-(2-bromophenyl)ureido]-3-methylphenylacetateYield 113.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of tert-butyl 4-amino-3-methylphenylacetate (780 mg, 3.30 mmol), 2-bromo phenyl isocyanate (0.41 ml, 3.30 mmol) in THF (7 ml) was added Et3 N (0.092 ml, 0.66 mmol) at room temperature. After 3 h stirring, the reaction mixture was concentrated in vacuo. The residue was triturated by the addition of n-hexane, to give tert-butyl 4-[N′-(2-bromophenyl) ureido]-3-methylphenylacetate (1.57 g, 93%) as a pale yellow powder. mp 138–145° C. (dec.); 1H-NMR (CDCl3) δ 1.44 (s, 9H), 2.33 (s, 3H), 3.51 (s, 2H), 6.90 (dt, J=9.0, 1.4 Hz, 1H), 6.98 (br, 1H), 7.18–7.31 (m, 4H), 7.39 (dd, J=8.1, 2.9 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 8.22 (d, J=8.3 Hz, 2H); Anal. Calcd for C20H22BrN2O3.0.2H2O: C, 56.80; H, 5.58; N, 6.62. Found: C, 56.85; H, 5.42; N, 6.62.

Workup

  1. additionwas added Et3 N (0.092 ml, 0.66 mmol) at room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was triturated by the addition of n-hexane

Sources & evidence

ORD record
ord-95cb6f96d9bb47038449f42ac62d1f53
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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