3,4,5-Trichloroaniline → HCID 178512051, compound

HRID 1981840Notes

Reaction equation

HRID 1981840 reaction equation
[CH3:1][N:2](N=O)[C:3]([NH:5][N+:6]([O-:8])=[O:7])=[NH:4].[Cl:11][C:12]1[CH:13]=C([CH:16]=[C:17]([Cl:20])[C:18]=1[Cl:19])N.[OH-].[Na+]>C(O)C>[N+:6]([NH:5][C:3]([NH:2][C:1]1[CH:13]=[C:12]([Cl:11])[C:18]([Cl:19])=[C:17]([Cl:20])[CH:16]=1)=[NH:4])([O-:8])=[O:7]

Participants

5

Reactant 3

HCID 124693,4,5-TrichloroanilineHCID 14798Sodium HydroxideHCID 135436526N-Methyl-N'-nitro-N-nitrosoguanidine2×

Product 1

HCID 178512051HCID 178512051, compoundYield 25.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a slurry of N-methyl-N-nitroso-N'-nitroguanidine 3.3 g (0.0225 mol) in 200 ml of a 50% aqueous ethanol mixture is added 5.0 g (0.025 mol) of 3,4,5-trichloroaniline. This mixture is heated to 40° C. for 72 hours and then treated with one equivalent of NaOH to decompose excess N-methyl-N-nitroso-N'-nitroguanidine. The mixture is then filtered and acidified with concentrated HCl to give 1.6 g of a yellow solid which, when recrystallized, gives 1.4 g of the desired product. The melting point of the product is 209.5° C. dec.

Workup

  1. filtrationThe mixture is then filtered

Sources & evidence

ORD record
ord-76da4b0f18914187a3fad3c701e743bb
Source dataset
uspto-grants-1986_06
Patent number
US04594092

Reaction notes

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