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

HRID 354360

Reaction equation

HRID 354360 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].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]=[C:25]=[O:26].CCN(CC)CC>C1COCC1>[Cl: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

5

Reactant 3

HCID 8471TriethylamineHCID 76833Chlorophenyl isocyanateHCID 23512173Tert-butyl 4-amino-3-methylphenylacetate

Product 1

HCID 23512001tert-butyl 4-[N'-(2-chlorophenyl)ureido]-3-methylphenylacetateYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of tert-butyl 4-amino-3-methylphenylacetate (1.00 g, 4.52 mmol), 2-chlorophenyl isocyanate (0.55 ml, 4.52 mmol) in THF (10 ml) was added Et3N (0.13 ml, 0.90 mmol) at room temperature. After 6 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-chlorophenyl)ureido]-3-methylphenylacetate (1.57 g, 93%) as a pale yellow powder. mp 104-106° C. (dec.); 1H-NMR (CDCl3) δ1.45 (s, 9H), 2.28 (s, 3H), 3.51 (s, 2H), 6.33 (br, 1H), 6.96 (t, J=7.6 Hz, 1H), 7.08 (br, 1H), 7.16-7.30 (m, 4H), 7.42 (m, 1H), 8.2 (d, J=8.1 Hz, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was triturated by the addition of n-hexane

Sources & evidence

ORD record
ord-7ffa5447e3ec4288b9792bdc518a6e34
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Linked notes

Loading…