Methyl Isocyanate → HCID 21441102, compound

HRID 329012Notes

Reaction equation

HRID 329012 reaction equation
C([N:3]([CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH2:4][CH2:5][NH2:6])=O.[H-].[Na+].[CH:16]([NH:18][CH2:19]CN)=[O:17].BrCC1C=CC=CN=1.CN=C=O>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:19][NH:18][C:16]([NH:6][CH2:5][CH2:4][NH:3][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:17]

Participants

8

Reactant 5

HCID 12228Methyl IsocyanateHCID 24758Sodium hydrideHCID 5642092-(Bromomethyl)pyridineHCID 13561311N-(2-Aminoethyl)formamideHCID 21441099HCID 21441099, compound

Product 1

HCID 21441102HCID 21441102, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-formyl-N-(2-pyridylmethyl)ethylene-diamine (prepared by adding sodium hydride to N-formylethylenediamine in dry dimethyl formamide, then reacting with 2-bromomethylpyridine at room temperature) and methyl isocyanate in dry chloroform is heated in a pressure vessel at 100° for 18 hours to give after cooling and removing the solvent N-methyl-N'-[2-((N"-formyl-N"-2-pyridylmethyl)amino)ethyl]urea. Acid hydrolysis by the procedure of Example 4 gives the title compound.

Workup

  1. customprepared
  2. temperatureis heated in a pressure vessel at 100° for 18 hours
  3. customto give
  4. temperatureafter cooling
  5. customremoving the solvent N-methyl-N'-[2-((N"-formyl-N"-2-pyridylmethyl)amino)ethyl]urea
  6. customAcid hydrolysis by the procedure of Example 4

Sources & evidence

ORD record
ord-9995bf78c17647adb701859ea5a7aa2b
Source dataset
uspto-grants-1977_04
Patent number
US04018928

Reaction notes

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