3-Pyridinemethanamine → Pyrinuron

HRID 1730919Notes

Reaction equation

HRID 1730919 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1>C1(C)C=CC=CC=1>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][NH:13][C:11]([NH:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[O:12])[CH:16]=1

Participants

4

Reactant 2

HCID 310183-PyridinemethanamineHCID 66012Benzene, 1-isocyanato-4-nitro-2×

Product 1

HCID 40813PyrinuronYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 415 g. of crude p-nitrophenyl isocyanate in 4.5 l. of toluene was stirred at room temperature. The mixture was filtered and 35 g. of insoluble impurity removed. The material in solution was 380 g. (2.32 mol) of purified p-nitrophenyl isocyanate. The solution was stirred under dry nitrogen, and 3-(aminomethyl)pyridine (250 g., 2.32 mol) was added dropwise. An exotherm to 40° C. was noted. The resulting thick suspension was stirred overnight and then vacuum filtered. The product was washed with hexane and dried in a vacuum oven at 60° C. overnight to give 610.7 g. melting at 220°-221.5° C. The product was a 98% yield of 1-(3-pyridylmethyl)-3-(4-nitrophenyl)urea. This product after recrystallization from 2-methoxyethanol melted with decomposition at 223°-225° C.

Workup

  1. filtrationThe mixture was filtered
  2. customof insoluble impurity removed
  3. customto 40° C.
  4. stirringThe resulting thick suspension was stirred overnight
  5. filtrationvacuum filtered
  6. washThe product was washed with hexane
  7. customdried in a vacuum oven at 60° C. overnight
  8. customto give 610.7 g

Sources & evidence

ORD record
ord-e28c4fc4d8bb4d3a9593d37a0004b69a
Source dataset
uspto-grants-1976_11
Patent number
US03994905

Reaction notes

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