Nitric Acid → HCID 178485126, compound

HRID 1973122Notes

Reaction equation

HRID 1973122 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][C:11]([NH:13][C:14]([NH:16][CH3:17])=[NH:15])=[NH:12].S(=O)(=O)(O)O.[N+:23]([O-])([OH:25])=[O:24].[OH-].[Na+]>O>[N+:23]([C:7]1[CH:8]=[C:3]([Cl:2])[C:4]([NH:10][C:11]([NH:13][C:14]([NH:16][CH3:17])=[NH:15])=[NH:12])=[C:5]([Cl:9])[CH:6]=1)([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 944Nitric Acid2×HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 178485124HCID 178485124, compound

Product 1

HCID 178485126HCID 178485126, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

1-(2,6-Dichlorophenyl)-5-methylbiguanide hydrochloride (14 g) is added to concentrated sulfuric acid (18 ml) and stirred for 5 minutes. Concentrated nitric acid (Sp. G. 1.51) (2.5 ml) is added dropwise, maintaining the temperature between 30° and 40° by water cooling if necessary. After addition of the nitric acid is complete, the mixture is stirred for 10 minutes, then poured into water. The mixture is made alkaline with sodium hydroxide, then extracted with ether. The ether extract is washed, dried (Na2SO4), evaporated and the residue crystallized from aqueous methanol to give 1-(4-nitro-2,6-dichlorophenyl)-5-methylbiguanide.

Workup

  1. stirringthe mixture is stirred for 10 minutes
  2. extractionextracted with ether
  3. extractionThe ether extract
  4. washis washed
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customthe residue crystallized from aqueous methanol

Sources & evidence

ORD record
ord-5936d16bbacc479abceac300d81a2af7
Source dataset
uspto-grants-1976_12
Patent number
US03996232

Reaction notes

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