Tributylamine → Pyrinuron

HRID 648068

Reaction equation

HRID 648068 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:15])OCC)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:16][CH2:17][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.C(N(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([NH:16][CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:15])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 7622TributylamineHCID 310183-PyridinemethanamineHCID 230135p-Nitrophenylurethane

Product 1

HCID 40813PyrinuronYield 95.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4.22 g (0.02 mole) of ethyl N-(4-nitrophenyl)carbamate, 1.80 g (0.0167 mole) of 3-aminomethyl-pyridine and 3.18 g (0.0173 mole) of tributylamine are dissolved in 25 ml of dry toluene, and the mixture is boiled for 5 hours. The separated product is filtered off, washed twice with 10 ml of acetone, each, and dried. 4.33 g (85.1%) of N-(4-nitrophenyl)-N'-(3-pyridylmethyl)-urea are obtained; m.p.: 222°-224° C. (the authentic sample melts at 223°-225° C.).

Workup

  1. filtrationThe separated product is filtered off
  2. washwashed twice with 10 ml of acetone
  3. customeach, and dried

Sources & evidence

ORD record
ord-ee0b2ccf7d3a4f2f80380ae99f558673
Source dataset
uspto-grants-1983_10
Patent number
US04410697

Linked notes

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