Methyl formate → Formamide

HRID 53365

Reaction equation

HRID 53365 reaction equation
[CH:1]([O:3][CH3:4])=[O:2].[C]=O.[C:7]([CH2:10][CH:11](C)[C:12]([O:14][CH3:15])=[O:13])(=[O:9])[NH2:8]>CO>[CH3:7][CH:10]([CH2:11][C:12]([O:14][CH3:15])=[O:13])[C:1]([O:3][CH3:4])=[O:2].[CH:7]([NH2:8])=[O:9]

Participants

6

Reactant 3

HCID 7865Methyl formateHCID 11768702Methyl 3-carbamoylisobutyrateHCID 178418416HCID 178418416, compound2×

Product 2

HCID 713FormamideHCID 15350Butanedioic acid, 2-methyl-, 1,4-dimethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The procedure in Example 3 (3) was repeated to proceed with heating stirring reaction except that in place of 180 g of methyl formate and 96 g of methanol, 200 g of methanol was charged in the autoclave and carbon monoxide was pressurized into the autoclave so as to maintain the internal pressure at 40 kg/cm2G. After the temperature of the content in the autoclave reached 60° C., carbon monoxide was fed in the autoclave so as to maintain the internal pressure at 40 kg/cm2G to proceed with the reaction for 3 hours. Subsequently, the content therein was cooled, internal pressure was gradually lowered to atmospheric pressure, and the reaction product was taken out. As a result of analysis therefor, the conversion of methyl 3-carbamoylisobutyrate was 81.4% and there were obtained dimethyl methylsuccinate at a selectivity of 95.7% and formamide at a selectivity of 94.4%, each based on the reacted methyl 3-carbamoylisobutyrate.

Workup

  1. temperaturewith heating
  2. temperatureto maintain the internal pressure at 40 kg/cm2G
  3. customreached 60° C.
  4. temperatureto maintain the internal pressure at 40 kg/cm2G
  5. customto proceed with the reaction for 3 hours
  6. temperatureSubsequently, the content therein was cooled
  7. customAs a result of analysis

Sources & evidence

ORD record
ord-e5055da4b54a4b05b2c5db3de2eb6879
Source dataset
uspto-grants-1997_04
Patent number
US05618953

Linked notes

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