Hydrochloric Acid → HCID 13455781, compound

HRID 1701077Notes

Reaction equation

HRID 1701077 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]([NH:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:4].C=O.S(Cl)(Cl)=O.Cl.S(=O)=O.[CH:23](Cl)(Cl)[Cl:24]>>[CH3:1][N:2]([CH3:12])[C:3]([N:5]([CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:23][Cl:24])=[O:4]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 1119Sulfur DioxideHCID 6212Chloroform2×HCID 24386Thionyl ChlorideHCID 350289ethyl 2-(dimethylcarbamoylamino)acetate

Product 1

HCID 13455781HCID 13455781, compound

Procedure

A reaction flask was charged with 100 cubic centimeters (cc) of chloroform, 45.4 grams (g) (0.26 mole) of N,N-dimethyl-N'-carboethoxymethylurea, and 9.0 g (0.3 mole) of paraformaldehyde. While the mixture was stirred continuously at room temperature, 35.4 g (21.4 cc, 0.3 mole) of thionyl chloride in a concentrated chloroform solution was added dropwise. A rise in temperature to 34° C. was observed. Hydrogen chloride and sulfur dioxide gases evolving from the reaction mixture were trapped in a caustic solution. The product was isolated by evaporation of the solvent, to provide 53.4 g, representing essentially full conversion. The structure as shown above was confirmed by proton resonance and mass spectrometry. The refractive index of the product was nD30 =1.4782.

Workup

  1. customto 34° C.
  2. customThe product was isolated by evaporation of the solvent
  3. customto provide 53.4 g

Sources & evidence

ORD record
ord-a1df2e29706644b5a5b2b6d270364e0e
Source dataset
uspto-grants-1980_03
Patent number
US04191552

Reaction notes

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