Methanol → HCID 178479534, compound

HRID 1639119Notes

Reaction equation

HRID 1639119 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15](=[NH:18])[NH:16][OH:17])=[CH:12][CH:11]=2)=[CH:6][C:5]=1[C:19]([F:22])([F:21])[F:20])([O-:3])=[O:2].[ClH:23].OC1C=CC(C2OC(C(=N)NO)=CC=2)=CC=1C(F)(F)F.CO.CO.Cl>C(OCC)C>[ClH:23].[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:14][C:13]([C:15](=[NH:18])[NH:16][OH:17])=[CH:12][CH:11]=2)=[CH:6][C:5]=1[C:19]([F:22])([F:20])[F:21])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 21893726Hydrochloride methanolHCID 178479535HCID 178479535, compoundHCID 178513267HCID 178513267, compound

Product 1

HCID 178479534HCID 178479534, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.3 g (0.008 mole) of D was stirred with 75 ml of abs. EtOH, 0.61 g (0.0088 mole) of hydroxylamine hydrochloride and 0.49 g (0.0088 mole) of crushed potassium hydroxide. The brown suspension was refluxed for 2 hours and then sat at room temperature overnight. The suspension was poured into 500 ml of water and an orange solid instantly precipitated out. The suspension continued to stir several minutes and then was filtered and the solid was air dried for 5 hours. The yield was 2.3 g (91% yield) of 5-(4-nitro-3-trifluoromethylphenyl)-N-hydroxy-2-furancarboximidamide (E1). 1 g of E1 was converted to its HCl salt (E2) using MeOH, MeOH/HCl, ethyl ether. The product was a tan solid which was dried at 100° in vacuum overnight. The IR, NMR and MS were consistent with structure of E2, and the m.p. was 221° with decomposition.

Workup

  1. customwas dried at 100° in vacuum overnight

Sources & evidence

ORD record
ord-165751e862d64ac2af369c34b2afb41b
Source dataset
uspto-grants-1989_11
Patent number
US04882354

Reaction notes

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