Formaldehyde → isopropyl N-(methylaminomethyl)carbamate hydrochloride

HRID 2049494

Reaction equation

HRID 2049494 reaction equation
[ClH:1].[CH3:2][NH2:3].[CH2:4]=O.[C:6](=[O:12])([O:8][CH:9]([CH3:11])[CH3:10])[NH2:7]>C(O)C>[ClH:1].[CH3:2][NH:3][CH2:4][NH:7][C:6](=[O:12])[O:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 15628Isopropyl carbamateHCID 6364545Methylamine hydrochloride

Product 1

HCID 12511010isopropyl N-(methylaminomethyl)carbamate hydrochlorideYield 77.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 50 ml of ethanol, 20.3 g (0.3 mole) of methylamine hydrochloride and 30.9 g (0.36 mole) of 37% formaldehyde aqueous solution were added and the mixture was warmed to 35°-40° C. Then, a solution prepared by dissolving 30.9 g (0.3 mole) of isopropyl carbamate in 150 ml of ethanol was added dropwise to the mixture with stirring maintaining the said temperature. After the dropwise addition of the solution, stirring was continued for 1 hour with heating and then the solvent was removed by distillation under reduced pressure. The residue was recrystallized from ethanol to give 42.7 g of isopropyl N-(methylaminomethyl)carbamate hydrochloride having a melting point of 163°-164° C. in yield of 77.8%. ##STR5##

Workup

  1. temperaturethe mixture was warmed to 35°-40° C
  2. customThen, a solution prepared
  3. additionwas added dropwise to the mixture
  4. temperaturemaintaining the said temperature
  5. additionAfter the dropwise addition of the solution
  6. stirringstirring
  7. temperaturewith heating
  8. customthe solvent was removed by distillation under reduced pressure
  9. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-280fc069745e431a8d0dd3daa014f1cd
Source dataset
uspto-grants-1980_04
Patent number
US04197410

Linked notes

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