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

HRID 350440Notes

Reaction equation

HRID 350440 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]>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

4

Reactant 2

HCID 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 Et3 N (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) δ 3.58 (s, 3H), 3.71 (s, 2H), 7.04 (m, 3M), 7.18 (dd, J=8.5, 2.0 Hz, 1H), 7.27–7.39 (m, 3H), 8.07 (m, 2M); MS (ESI) m/z 353 (M++1), 355 (M++3), 357 (M++5).

Workup

  1. additionwas added Et3 N (0.14 ml, 1.00 mmol) at room temperature
  2. stirringstirred 17 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customThe residue was triturated by the addition of n-hexane

Sources & evidence

ORD record
ord-d58ff9bad144456a81df6cc770fcf39f
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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