Water → HCID 57802949, compound

HRID 1921079Notes

Reaction equation

HRID 1921079 reaction equation
[CH3:1][NH:2][C:3]([NH2:5])=[O:4].C[O-].[Na+].C(O[C:12](=[O:27])[CH:13]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)[C:14]([O:16]CC)=O)C.O>CN(C)C=O>[Cl:26][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][CH:13]1[C:12](=[O:27])[N:2]([CH3:1])[C:3](=[O:4])[NH:5][C:14]1=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 11719MethylureaHCID 10803022HCID 10803022, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 57802949HCID 57802949, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
130 °C

Procedure

Methylurea (1.18 g, 16.0 mmol) and freshly prepared sodium methoxide (1.04 g, 19.2 mmol) were combined in dimethylformamide (15 mL) and a solution of 2-(3-chlorobenzyl)malonic acid diethyl ester (2.85 g, 10.0 mmol) in dimethylformamide (5 mL) was added. The reaction temperature was raised to 130° C. for 2 hours and then cooled to ambient temperature before water was added and the solution acidified with 2N HClaq. The resulting solid was filtered then washed with water and the dried to afford the product as a white solid, 840 mg. LC-MS: RT=2.87 mins, 267 (M+H)+ 265 (M−H)−.

Workup

  1. additionwas added
  2. filtrationThe resulting solid was filtered
  3. washthen washed with water
  4. customthe dried

Sources & evidence

ORD record
ord-267bfc33030545c58691d80386ef1c4d
Source dataset
uspto-grants-2012_05
Patent number
US08173664B2

Reaction notes

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