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

HRID 354374Notes

Reaction equation

HRID 354374 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].[CH3:14][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[CH3:14])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 691942-Tolyl isocyanate2×HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 23512346methyl 3-chloro-4-[N'-(2-methylphenyl)ureido]phenylacetateYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-amino-3-chlorophenylacetate (1.00 g, 5.01 mmol) and 2-methylphenyl 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-methylphenyl 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-methylphenyl)ureido]phenylacetate (1.23 g, 74%) as a colorless powder. 1H-NMR (CDCl3) δ2.34 (s, 3H, 3.54 (s, 2H), 3.68 (s, 3H), 6.24 (br, 1H), 6.99 (br, 1H), 7.15 (dd, J=8.3, 2.0 Hz, 1H), 7.21-7.31 (m, 5H), 7.44 (d, J=7.6 Hz, 1H), 8.20 (d, J=8.5 Hz, 1H); MS (ESI) m/z 333 (M++1), 335 (M++3).

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-02fc90ca7fe847019d48591566334dbb
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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