Water → Pyrinuron

HRID 648070

Reaction equation

HRID 648070 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:14])OC)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.O>C1(C)C(C)=CC=CC=1.CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11]([NH:15][CH2:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)=[O:14])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 962WaterHCID 310183-PyridinemethanamineHCID 74752Carbamic acid, N-(4-nitrophenyl)-, methyl ester

Product 1

HCID 40813PyrinuronYield 88.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 7237O-XyleneSolvent2×

Procedure

A mixture of 5.88 g (0.03 mole) of methyl N-(4-nitrophenyl)-carbamate, 2.70 g (0.025 mole) of 3-aminomethyl-pyridine, 9.6 ml of Gemanin CS 302D (a mixture of N,N-dimethyl-C10-18 alkylamines sold by the firm Hoechst AG) and 50 ml of xylene is filled into a flask equipped with a 20 cm Vigreux column and a Dean-Stark trap, and the mixture is boiled for 2 hours. During this period 6 ml of a mixture of water, methanol and xylene accumulate in the trap. The mixture is filtered when hot, the crystalline end-product is washed twice with 5 ml of hot xylene, each, and then with a few amount of acetone and dried. 6.0 g (88.2%) of N-(4-nitrophenyl)-N'-(3-pyridylmethyl)-urea are obtained; m.p.: 223°-225° C.

Workup

  1. additionis filled into a flask
  2. customequipped with a 20 cm Vigreux column
  3. filtrationThe mixture is filtered when hot
  4. washthe crystalline end-product is washed twice with 5 ml of hot xylene
  5. dry with materialeach, and then with a few amount of acetone and dried

Sources & evidence

ORD record
ord-1f89c00beb094472a378de27ef9b1a5b
Source dataset
uspto-grants-1983_10
Patent number
US04410697

Linked notes

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