Sodium Hydroxide → HCID 136333558, compound

HRID 1735909Notes

Reaction equation

HRID 1735909 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[C:15]([CH:16]=O)=[CH:14][NH:13][C:12]1=[S:18].Cl.[NH2:20][OH:21].[OH-].[Na+]>C(O)C.O>[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[N:11]1[C:15]([CH:16]=[N:20][OH:21])=[CH:14][NH:13][C:12]1=[S:18]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 19699564HCID 19699564, compound

Product 1

HCID 136333558HCID 136333558, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 3-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-4-carbaldehyde (0.25 g, 1.0 mmol), hydroxylamine hydrochloride (0.09 g, 1.3 mmol) and sodium hydroxide (0.064 g, 1.6 mmol) in 2 mL of ethanol and 2 mL of water was stirred at 60° C. for 1 hour. The mixture was cooled giving a crystalline material. The material was isolated by filtration and dried. The filtrate was stirred with ethyl acetate giving more crystalline material. The material was isolated by filtration and dried. Combining the crystalline material gave 1-(1,2,3,4-tetrahydronaphthalen-2-yl)-2-thioxo-2,3-dihydro-1H-imidazole-5-carbaldehyde oxime (0.186 g, 0.68 mmol).

Workup

  1. temperatureThe mixture was cooled
  2. customgiving a crystalline material
  3. customThe material was isolated by filtration
  4. customdried
  5. stirringThe filtrate was stirred with ethyl acetate giving more crystalline material
  6. customThe material was isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-9a2f499d35cf4aac9287e99985ca7a25
Source dataset
uspto-grants-1996_07
Patent number
US05538988

Reaction notes

Loading…