1,3-Dichloro-2-isocyanatobenzene → tert-butyl 4-[N'-(2,6-dichlorophenyl)ureido]-3-methylphenylacetate

HRID 350434Notes

Reaction equation

HRID 350434 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]>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

4

Reactant 2

HCID 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 Et3 N (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) δ 1.45 (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=7.8 Hz, 1H).

Workup

  1. additionwas added Et3 N (0.24 ml, 1.70 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-aca68f340c3f43f7aa54fe13a35c57ad
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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