Triethylamine → tert-butyl 4-[N'-(2,6-dichlorophenyl)ureido]-3-methylphenylacetate

HRID 354371Notes

Reaction equation

HRID 354371 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]=[C:20]([Cl:24])[C:19]=1[N:25]=[C:26]=[O:27].CCN(CC)CC>C1COCC1>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=1[NH:25][C:26](=[O:27])[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 6045371,3-Dichloro-2-isocyanatobenzeneHCID 23512173Tert-butyl 4-amino-3-methylphenylacetate

Product 1

HCID 23512351tert-butyl 4-[N'-(2,6-dichlorophenyl)ureido]-3-methylphenylacetateYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 4-amino-3-methylphenylacetate (1.88 g, 8.51 mmol), 2,6-dichlorophenyl isocyanate (1.60 g, 8.51 mmol) in THF (40 ml) was added Et3N (0.24 ml, 1.70 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′-(2,6-dichlorophenyl)ureido]-3-methylphenylacetate (2.58 g, 74%) as a colorless powder. mp 243-244° C. (dec.); 1H-NMR (CDCl3) δ1.45 (s, 9H), 2.30 (s, 3H), 3.49 (s, 2H), 6.24 (s, 2H), 7.12-7.16 (m, 3H), 7.35 (d, J=8.3 Hz, 2H), 7.51 (d, J 7.8H, 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-1189e5d8c2ab404ba698615b5c8aeaca
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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