Methyl chloroformate → N-carbomethoxy-O-methylisourea

HRID 1729572Notes

Reaction equation

HRID 1729572 reaction equation
S(O)(O)(=O)=O.[CH3:6][O:7][C:8](=[NH:10])[NH2:9].Cl[C:12]([O:14][CH3:15])=[O:13].[OH-].[Na+]>O>[NH2:10][C:8](=[N:9][C:12](=[O:13])[O:14][CH3:15])[O:7][CH3:6]

Participants

5

Reactant 3

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

Product 1

HCID 53429793N-carbomethoxy-O-methylisourea

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 52 parts of 2-methylpseudourea hydrogen sulfate in 250 parts of water at 0°-5° C. is added 31 parts of methyl chloroformate followed by dropwise addition of 74 parts of 50% sodium hydroxide. The reaction mass is stirred at room temperature for 3 hours and then extracted with methylene chloride. The methylene chloride extract is dried and the solvent evaporated. The residue is triturated with hexane to give 23 parts of methyl N-(1-amino-1-methoxymethylene)carbamate melting at 36°-39.5° C.

Workup

  1. extractionextracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. customis dried
  4. customthe solvent evaporated
  5. customThe residue is triturated with hexane

Sources & evidence

ORD record
ord-5a92dd935b5346c6a226891e374ba90c
Source dataset
uspto-grants-1976_11
Patent number
US03989501

Reaction notes

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