Formaldehyde → HCID 11321022, compound

HRID 989434Notes

Reaction equation

HRID 989434 reaction equation
C=O.[NH2:3][N:4]([CH2:9][CH2:10][OH:11])[C:5](=[O:8])[O:6][CH3:7].[C:12]1(C)C=CC(S(O)(=O)=O)=CC=1.S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl>[O:11]1[CH2:10][CH2:9][N:4]([C:5]([O:6][CH3:7])=[O:8])[NH:3][CH2:12]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 24083Sulfuric acid magnesium salt (1:1)HCID 11252029HCID 11252029, compound

Product 1

HCID 11321022HCID 11321022, compoundYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
42 °C

Procedure

At 22° C., 22.4 g (0.746 mol) of paraformaldehyde were added with stirring, over a period of 2 min to a mixture of 100 g (0.746 mol) of methyl N-amino-N-2-hydroxyethylcarbamate in 1500 ml of methylene chloride. After addition of 8.5 g (0.045 mol) of p-toluenesulfonic acid, the mixture was stirred at 42° C. for 21 h, until the precipitate had dissolved, and was then cooled to 20° C., and magnesium sulfate was added. The mixture was filtered and the filtrate was concentrated under reduced pressure. This gave 111.8 g of the title compound as a colorless resin with a GC purity of 85%, corresponding to a yield of 85.8% of theory.

Workup

  1. dissolutionhad dissolved
  2. temperaturewas then cooled to 20° C.
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9b5668dcceb848afbe17850441d57acc
Source dataset
uspto-grants-2003_10
Patent number
US06639070B1

Reaction notes

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