Hydroxylamine → HCID 178485196, compound

HRID 1076126

Reaction equation

HRID 1076126 reaction equation
[C:1]1([NH:7][C:8]([NH:10][CH3:11])=S)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:13][OH:14].[OH-].[K+].N=C=N.NO>CCOCC.CO>[C:1]1([NH:7][C:8]([NH:10][CH3:11])=[N:13][OH:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 787HydroxylamineHCID 14797Potassium HydroxideHCID 160435CarbodiimideHCID 443297Hydroxyamine hydrochlorideHCID 6982941-Methyl-3-phenylthiourea

Product 1

HCID 178485196HCID 178485196, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 6.6 g (0.04 mole) of 1-phenyl-3-methylthiourea and 17.3 g (0.08 mole) of yellow mercuric oxide in 50 ml of ether was stirred vigorously at room temperature for 0.5 hour. The thick slurry was diluted with additional ether and filtered. To the filtrate was added all at once a solution of hydroxylamine prepared by treating 3.5 g (0.05 mole) of hydroxylamine hydrochloride in 50 ml of methanol at 0° with 2.8 g (0.05 mole) of potassium hydroxide (filtered after 0.5 hour to remove potassium chloride). The ether-methanol solution of the carbodiimide and hydroxylamine was stirred for 0.5 hour, then the solvent was removed at reduced pressure. The residue was dissolved in dilute hydrochloric acid and extracted with methylene chloride to remove neutral impurities. The aqueous layer was then made basic with sodium hydroxide. Extraction with methylene chloride and removal of the solvent gave the crude product. It was recrystallized from methylene chloride/hexane to give 1.3 g of white 1-phenyl-3-methyl-2-hydroxyguanidine, mp 95°-6°; nmr (CDCl3): δ 2.7 (s, 3); 6.9-7.4 (m, 5); 4-7 (very broad, 3). IR (chloroform solution): both OH and NH present. In the antitetrabenazine test, this compound gave a ptosis ED50 of 12.2 mg/kg and exploratory ED50 of > 81 mg/kg.

Workup

  1. filtrationfiltered
  2. additionTo the filtrate was added all at once a solution of hydroxylamine
  3. customprepared
  4. customthe solvent was removed at reduced pressure
  5. dissolutionThe residue was dissolved in dilute hydrochloric acid
  6. extractionextracted with methylene chloride
  7. customto remove neutral impurities
  8. extractionExtraction
  9. customwith methylene chloride and removal of the solvent
  10. customgave the crude product
  11. customIt was recrystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-364d7cb98b944ca4908db868e5719fbc
Source dataset
uspto-grants-1976_05
Patent number
US03954995

Linked notes

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