Dichloromethane → 1,3-dimethoxycarbonyl-O-methylisourea

HRID 496833

Reaction equation

HRID 496833 reaction equation
[C:1]([O-:4])([O-:3])=O.[Na+].[Na+].S(O)(O)(=O)=O.[CH3:12][O:13][C:14](=[NH:16])[NH2:15].Cl[C:18]([O:20][CH3:21])=[O:19].[OH-].[Na+].[CH2:24](Cl)Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:24][O:3][C:1]([NH:16][C:14](=[N:15][C:18]([O:20][CH3:21])=[O:19])[O:13][CH3:12])=[O:4]

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)

Product 1

HCID 853487891,3-dimethoxycarbonyl-O-methylisourea

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

A three-neck flask fitted with a mechanical stirrer was charged with H2O (1.1 L), CH2Cl2 (1 L) and Na2CO3 (254.4 g, 2.4 mol) and the mixture chilled to ca 5° C. To the chilled mixture was then added the O-methylisourea hydrogen sulfate from above, tetrabutylammonium bromide (0.5 g) and methyl chloroformate (556 mL, 7.2 mol). The mixture was stirred vigorously and 25% NaOH (144 g in ca. 600 mL) was added over 0.5 h. After the last addition, the mixture was stirred for an additional 2 h and then filtered through Celite to remove inorganic salts (Na2SO4). The layers were separated and the organic layer dried (Na2SO4), filtered and concentrated to give the title compound as a thick syrup. The syrup was dried in vacuo overnight during which time it solidified to give 114.7 g (0.6 mol. 53%) of 1,3-dimethoxycarbonyl-O-methylisourea.

Workup

  1. customA three-neck flask fitted with a mechanical stirrer
  2. temperaturethe mixture chilled to ca 5° C
  3. additionAfter the last addition
  4. stirringthe mixture was stirred for an additional 2 h
  5. filtrationfiltered through Celite
  6. customto remove inorganic salts (Na2SO4)
  7. customThe layers were separated
  8. dry with materialthe organic layer dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-85697c4cfef349d48d942fc9e44a1f8b
Source dataset
uspto-grants-2005_09
Patent number
US06946554B2

Linked notes

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