Triethylamine → methyl 3-chloro-4-[N'-(2-chlorophenyl)ureido]phenylacetate

HRID 354376

Reaction equation

HRID 354376 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[Cl:13].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[N:21]=[C:22]=[O:23].CCN(CC)CC>C1COCC1>[Cl:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:7][C:2]=1[NH:1][C:22]([NH:21][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[Cl:14])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76833Chlorophenyl isocyanate2×HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 23512406methyl 3-chloro-4-[N'-(2-chlorophenyl)ureido]phenylacetateYield 76.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-amino-3-chlorophenylacetate (1.00 g, 5.01 mmol) and 2-chlorophenyl isocyanate (0.60 ml, 5.01 mmol) in THF (20 ml) was added Et3N (0.14 ml, 1.00 mmol) at room temperature. After 1 day stirring, 2-chlorophenyl isocyanate (0.60 ml, 5.01 mmol) was added to the reaction mixture and stirred 17 h. The reaction mixture was concentrated in vacuo. The residue was triturated by the addition of n-hexane to give methyl 3-chloro-4-[N′-(2-chlorophenyl)ureido]phenylacetate (1.35 g, 76%) as a colorless powder. 1H-NMR (CDCl3) δ3.58 (s, 3H), 3.71 (s, 2H), 7.04 (m, 3H), 7.18 (dd, J=8.5, 2.0 Hz, 1H), 7.27-7.39 (m, 3H), 8.07 (m, 2H); MS (ESI) m/z 353 (M++1), 355 (M++3), 357 (M++5).

Workup

  1. stirringstirred 17 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was triturated by the addition of n-hexane

Sources & evidence

ORD record
ord-c097c8b9b35247f399ba14bf72666327
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Linked notes

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