Methylamine → 1-(5-Bromo-2-chlorobenzyl)-3-methylurea

HRID 1408417Notes

Reaction equation

HRID 1408417 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH2:8][NH2:9])[CH:7]=1.C([C:18]1[NH:19][CH:20]=CN=1)(C1NC=CN=1)=O.CN.C1C[O:28]CC1>ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([CH2:8][NH:9][C:20]([NH:19][CH3:18])=[O:28])[CH:7]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 43378979(5-Bromo-2-chlorophenyl)methanamine

Product 1

HCID 671513081-(5-Bromo-2-chlorobenzyl)-3-methylurea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-2-chlorobenzenemethanamine (i.e. the product of Synthesis Example 2, Step A) (1.3 g, 5.5 mmol) in dichloromethane (25 mL) at 0° C. was added carbonyl diimidazole (1.4 g, 8.6 mmol). The reaction mixture was stirred at room temperature for 1 h. Then the reaction mixture was cooled to 0° C., a solution of methylamine in THF (2 M, 3.0 mL, 6.0 mmol) was added, and the reaction mixture was stirred at room temperature for 4 h. The reaction mixture was filtered, and the solid residue was washed with pentane to provide the title product (1.0 g).

Workup

  1. temperatureThen the reaction mixture was cooled to 0° C.
  2. stirringthe reaction mixture was stirred at room temperature for 4 h
  3. filtrationThe reaction mixture was filtered
  4. washthe solid residue was washed with pentane

Sources & evidence

ORD record
ord-2455f8029d9f45a18e984e14a4530097
Source dataset
uspto-grants-2014_12
Patent number
US08921360B2

Reaction notes

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