Dichloromethane → HCID 18976542, compound

HRID 2393670Notes

Reaction equation

HRID 2393670 reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][N:8]1[C:12](=[O:13])[CH2:11][N:10]([CH2:14]CC(O)=O)[C:9]1=[O:19].C(Cl)Cl>CN(C)C=O>[CH3:7][N:8]1[C:12](=[O:13])[CH2:11][N:10]([CH2:14][CH2:1][C:2]([Cl:4])=[O:3])[C:9]1=[O:19]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 18976546HCID 18976546, compound

Product 1

HCID 18976542HCID 18976542, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

340.9 g (2.6857 mol) of oxalyl chloride are added dropwise over the course of 18 minutes at an internal temperature of 19°-23° C. to a solution of 100.0 g (0.537 mol) of 3-(3-methyl-2,4-dioxoimidazolidin-1-yl)propionic acid, synthesized as described in Example 6, 350 ml of methylene chloride and 1 ml of dimethyl formamide, and the mixture is subsequently stirred at room temperature for 5 hours and 10 minutes. When the reaction is complete, the reaction mixture is evaporated in a rotary evaporator, the residue is stripped 3 times at 50° C. under reduced pressure with 100 ml of toluene in each case, and the residue is dried at 60° C./0.1 mbar to constant weight, giving 106.1 g (97.3% of theory) of solid, brownish 3-(3-methyl-2,4-dioxoimidazolidin-1-yl)propionyl chloride having the following analytical data:

Workup

  1. customsynthesized
  2. customthe reaction mixture is evaporated in a rotary evaporator
  3. customat 50° C.
  4. customthe residue is dried at 60° C./0.1 mbar to constant weight

Sources & evidence

ORD record
ord-8f4329ab6dc843798de40171123fabf9
Source dataset
uspto-grants-1998_09
Patent number
US05807927

Reaction notes

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