Triethylamine → methyl 4-[N'-(2-bromophenyl)ureido]-3-chlorophenylacetate

HRID 354378Notes

Reaction equation

HRID 354378 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].[Br: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>[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][C:22](=[O:23])[NH: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]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1370972-Bromophenyl isocyanate2×HCID 13616273Methyl 2-(4-amino-3-chlorophenyl)acetate

Product 1

HCID 23512063methyl 4-[N'-(2-bromophenyl)ureido]-3-chlorophenylacetateYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl 4-amino-3-chlorophenylacetate (1.00 g, 5.01 mmol) and 2-bromophenyl isocyanate (0.62 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-bromophenyl isocyanate (0.60 ml, 5.01 mmol) was added to the reaction mixture and stirred 24 h. The reaction mixture was concentrated in vacuo. The residue was triturated by the addition of n-hexane to give methyl 4-[N′-(2bromophenyl)ureido]-3-chlorophenylacetate (1.34 g, 67%) as a colorless powder. 1H-NMR (CDCl3) δ3.58 (s, 3H), 3.70 (s, 2H), 6.98 (m, 3H), 7.19 (dd, J=8.3, 1.9 Hz, 1H), 7.32 (m, 1H), 7.51 (m, 2H),k 8.05 (m, 1H); MS (ESI) m/z 398 (M++1), 400 (M++3), 402 (M++5).

Workup

  1. stirringstirred 24 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-88e3238f019543ffa644f66af6ae268a
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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