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Chloroacetic Acid → HCID 15919477, compound

HRID 463661
Notes
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Reaction equation

HRID 463661 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]([CH3:10])=[C:6]([CH3:11])[C:5]1=[O:12].[Cl:13][CH2:14][C:15](O)=[O:16].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[Cl:13][CH2:14][C:15]([O:1][CH2:2][CH2:3][N:4]1[C:8](=[O:9])[C:7]([CH3:10])=[C:6]([CH3:11])[C:5]1=[O:12])=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 300Chloroacetic AcidHCID 962Water2×HCID 1118Sulfuric AcidHCID 159194761-(2-Hydroxyethyl)-3,4-dimethyl-1H-pyrrole-2,5-dione

Product 1

HCID 15919477HCID 15919477, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

With stirring, 169.2 g (1 mole) of N-(2-hydroxyethyl)dimethylmaleimide, 113.4 g (1.2 moles) of chloroacetic acid and 11.8 g of concentrated sulfuric acid are heated to reflux in 1000 ml of toluene using a water separator. The formation of water ceases after about 2 hours and 18 ml have separated. The reaction solution is washed with saturated sodium bicarbonate solution and water. The organic phase is dried over magnesium sulfate and concentrated in a rotary evaporator at 40° C. The residue is dried for 2 hours at 60° C./0.1 mm, affording 206 g of a colourless liquid.

Workup

  1. custom18 ml have separated
  2. washThe reaction solution is washed with saturated sodium bicarbonate solution and water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. concentrationconcentrated in a rotary evaporator at 40° C
  5. customThe residue is dried for 2 hours at 60° C./0.1 mm

Sources & evidence

ORD record
ord-98274917f90b4eb29edf8696760b6703
Source dataset
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04544621

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes