Water → methyl N-(3-methylbutanimidoyl)carbamate

HRID 1248105Notes

Reaction equation

HRID 1248105 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[OH-].[K+].O.Cl.[C:10]([NH2:16])(=[NH:15])[CH2:11][CH:12]([CH3:14])[CH3:13]>C(Cl)Cl>[CH3:5][O:4][C:2]([NH:16][C:10](=[NH:15])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6586Methyl chloroformateHCID 14797Potassium HydroxideHCID 189679323-Methylbutanimidamide hydrochloride

Product 1

HCID 140338861methyl N-(3-methylbutanimidoyl)carbamateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

78.8 parts of methyl chloroformate and a mixture of 46.8 parts of potassium hydroxide in 215 parts of water are added via two inlets to a mixture of 113.8 parts of isovaleramidine hydrochloride in 530 parts of methylene chloride, at from 0° to 10° C., in the course of 25 minutes, while stirring. The mixture is stirred at 25° C. for 30 minutes, the phases are separated and the aqueous phase is extracted once with methylene chloride. The solvent is removed from the organic extract to give 123 parts (93.3% of theory) of N-methoxycarbonylisovaleramidine of melting point 82°-86° C.

Workup

  1. stirringThe mixture is stirred at 25° C. for 30 minutes
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted once with methylene chloride
  4. customThe solvent is removed from the
  5. extractionorganic extract

Sources & evidence

ORD record
ord-06cc097551514c399d9139fecfbf439b
Source dataset
uspto-grants-1985_06
Patent number
US04522763

Reaction notes

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