Water → Pyrinuron

HRID 648071

Reaction equation

HRID 648071 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=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 40813Pyrinuron

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

11.77 g (0.06 mole) of methyl N-(4-nitrophenyl)carbamate, 5.4 g (0.05 mole) of 3-aminomethyl-pyridine, 18.7 g (0.065 mole) of Genamin SH 302 D (a mixture of N,N-dimethyl-C16-18 alkylamines sold by the firm Hoechst AG) and 200 ml of toluene are introduced into the apparatus described in Example 4, and the mixture is boiled for 4 hours. During this period 15 ml of a mixture of water, methanol and toluene accumulate in the trap. The separated solid is filtered off, washed twice with 10 ml of hot toluene, and the resulting mixture is used as reaction medium in the above reaction. The mother liquor is recycled 10 times. The results of the individual cycles are summarized in Table 1.

Workup

  1. additionare introduced into the apparatus
  2. filtrationThe separated solid is filtered off
  3. washwashed twice with 10 ml of hot toluene
  4. customthe resulting mixture is used as reaction medium in the above reaction
  5. customThe results of the individual cycles

Sources & evidence

ORD record
ord-fbb6ea9090cb48c89a60c8b368dc1926
Source dataset
uspto-grants-1983_10
Patent number
US04410697

Linked notes

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