Hydrochloric Acid → 1,3-Dimethyl-1-(4-pyridylmethyl)-3-phenylurea

HRID 1164512Notes

Reaction equation

HRID 1164512 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:13][N:14]([CH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)[C:1]([N:6]([CH3:5])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:2]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 7515N-MethylanilineHCID 14798Sodium HydroxideHCID 81436N-Methylpyridine-4-methylamine

Product 1

HCID 205111751,3-Dimethyl-1-(4-pyridylmethyl)-3-phenylurea

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolvent3×HCID 8471TriethylamineSolvent

Procedure

Phosgene in toluene (50 ml, 121/2% solution was stirred at 0°-10° whilst a mixture of N-methylaniline (5.4 g) and triethylamine (15 ml) in dry chloroform (100 ml) was added slowly dropwise. On completion of the addition the mixture was stirred for 19 hours at room temperature, then cooled to 0°-10° whilst a solution of 4-(N-methylaminomethyl)pyridine (3.1 g) in dry chloroform (70 ml) was slowly added. The mixture was stirred at room temperature overnight followed by the cautious addition of 2 N hydrochloric acid (20 ml). After 1 hour, 5 N sodium hydroxide (12 ml) was added and the organic phase was separated, washed (H2O, 50 ml), dried (Na2CO3) and evaporated in vacuo to give a dark oil. The oil was dissolved in the minimum quantity of chloroform and chromatographed on a "Florisil" (Trademark) column eluted with chloroform. Appropriate fractions were identified by thin layer chromatography, combined and evaporated in vacuo to give 1,3-dimethyl-1-(4-pyridylmethyl)-3-phenylurea as a dark oil (3 g). The n.m.r. spectrum was compatible with the required structure.

Workup

  1. additionwas added slowly dropwise
  2. additionOn completion of the addition the mixture
  3. additionwas slowly added
  4. stirringThe mixture was stirred at room temperature overnight
  5. waitAfter 1 hour
  6. customthe organic phase was separated
  7. washwashed (H2O, 50 ml)
  8. dry with materialdried (Na2CO3)
  9. customevaporated in vacuo
  10. customto give a dark oil
  11. customchromatographed on a "Florisil" (Trademark) column
  12. washeluted with chloroform
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-efade34e950545af9f3ffb6309a5e56a
Source dataset
uspto-grants-1983_01
Patent number
US04370328

Reaction notes

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