[2,6-Dinitro-4-(trifluoromethyl)phenyl]hydrazine → HCID 21540613, compound

HRID 1075732Notes

Reaction equation

HRID 1075732 reaction equation
N#N.[CH3:3][N:4]([NH:6][C:7]1[C:12]([N+:13]([O-])=O)=[C:11]([Cl:16])[C:10]([C:17]([F:20])([F:19])[F:18])=[CH:9][C:8]=1[NH2:21])[CH3:5].[N+]([C:25]1C=C(C(F)(F)F)C=C([N+]([O-])=O)[C:30]=1NN)([O-])=O>[Pd].C(O)C>[NH2:13][C:12]1[C:7]2[N:6]([N:4]([CH3:5])[CH3:3])[C:25]([CH3:30])=[N:21][C:8]=2[CH:9]=[C:10]([C:17]([F:20])([F:19])[F:18])[C:11]=1[Cl:16]

Participants

5

Reactant 2

HCID 3755830[2,6-Dinitro-4-(trifluoromethyl)phenyl]hydrazineHCID 86733367HCID 86733367, compound

Product 1

HCID 21540613HCID 21540613, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 5.2g. of N2 -(dimethylamino)-4-chloro-3-nitro-5-trifluoromethyl-1,2-phenylenediamine (prepared by hydrogenation of the corresponding 3,5-dinitro-4-hydrazinobenzotrifluoride in the presence of palladium catalyst) and 7.5g. of ethyl methylcarboximidate hydrochloride in 60 ml. of ethanol was refluxed for 26 hours. The resultant 7-nitrobenzimidazole was separated by fractionation on a silica gel column and then hydrogenated in the presence of platinum oxide catalyst in dimethoxyethane-methanol to give the desired product (2.8g.) m.p. 173°-174°C.

Workup

  1. customThe resultant 7-nitrobenzimidazole was separated by fractionation on a silica gel column

Sources & evidence

ORD record
ord-e658f6ed65cb402d8b3818dc8abf7361
Source dataset
uspto-grants-1976_05
Patent number
US03954438

Reaction notes

Loading…