Hydroxyamine hydrochloride → HCID 178513441, compound

HRID 1763556Notes

Reaction equation

HRID 1763556 reaction equation
Cl.[N:2]1([NH:11][C:12](=[NH:15])SC)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.Cl.[NH2:17][OH:18].[O-]CC.[K+]>C(O)C>[OH:18][NH:17][C:12]([NH:11][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)=[NH:15]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 23670592Potassium ethoxideHCID 178504053HCID 178504053, compound

Product 1

HCID 178513441HCID 178513441, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10 g of 1-(indolin-1-yl)-2-methylisothiourea hydrochloride and 11.4 g of hydroxylamine hydrochloride were suspended in 240 ml of ethanol and were heated to the boil for one hour upon the addition of 6.9 g of potassium ethoxide. Upon cooling, the potassium chloride and the excess hydroxylamine hydrochloride were filtered off with suction and the filtrate was evaporated to dryness. The evaporation residue was partitioned between concentrated aqueous ammonia solution and methylene choride. The methylene chloride solution was dried over magnesium sulphate and evaporated to dryness. 1-hydroxy-3-(indolin-1-yl)guanidine was obtained as an evaporation residue and was crystallized upon the addition of acetic acid, as the acetate from ethanol/ether having a M.Pt. of 155° - 156°.

Workup

  1. temperatureUpon cooling
  2. filtrationthe potassium chloride and the excess hydroxylamine hydrochloride were filtered off with suction
  3. customthe filtrate was evaporated to dryness
  4. customThe evaporation residue was partitioned between concentrated aqueous ammonia solution and methylene choride
  5. dry with materialThe methylene chloride solution was dried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-f6bbb17747c04149b8a710116a7f9e60
Source dataset
uspto-grants-1978_09
Patent number
US04112111

Reaction notes

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