Sodium Hydroxide → HCID 20402696, compound

HRID 1980265Notes

Reaction equation

HRID 1980265 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[C:6]([C:14]1[C:15]([NH:21][C:22](=[O:25])[CH2:23]I)=[CH:16][N:17]([CH3:20])[C:18]=1[CH3:19])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>O.C(O)C>[C:6]([C:14]1[C:15]([NH:21][C:22](=[O:25])[CH2:23][NH:4][OH:1])=[CH:16][N:17]([CH3:20])[C:18]=1[CH3:19])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 20402707HCID 20402707, compound

Product 1

HCID 20402696HCID 20402696, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium hydroxide (64 g) was added to a solution of hydroxylamine hydrochloride (111 g) in water (370 ml) and the obtained solution was diluted with ethanol (3500 ml). N-(4-benzoyl-1,5-dimethyl(1H)pyrrol-3-yl)-2-iodoacetamide (124.5 g) was then added and the obtained suspension was stirred under nitrogen stream for about 48 hours. The reaction mixture was filtered in order to remove the salts and the filtrate was concentrated to dryness at the pump. The residue was washed with a small amount of water and crystallized from ethyl acetate yielding 82.5 g of the compound of the title. M.p. 140°-42° C.

Workup

  1. filtrationThe reaction mixture was filtered in order
  2. customto remove the salts
  3. concentrationthe filtrate was concentrated to dryness at the pump
  4. washThe residue was washed with a small amount of water
  5. customcrystallized from ethyl acetate yielding 82.5 g of the compound of the title

Sources & evidence

ORD record
ord-c344f08c91ec4804b2a17be78cd21e0f
Source dataset
uspto-grants-1985_04
Patent number
US04508730

Reaction notes

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