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

HRID 350438Notes

Reaction equation

HRID 350438 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]>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

4

Reactant 2

HCID 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 Et3 N (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) δ 2.34 (s, 3H), 3.54 (s, 2H), 3.68 (s, 3H), 6.24 (br, 1H1), 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. 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-7aa1a81e3bd3494a8e9c0b86bbb93c8e
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…