Water → alpha-[(hydroxyamino)iminomethyl]-N-(2,4,6-trimethoxyphenyl)-benzeneacetamide

HRID 1938749Notes

Reaction equation

HRID 1938749 reaction equation
Cl.[NH2:2][OH:3].C(N(CC)CC)C.[C:11]([CH:13]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:14]([NH:16][C:17]1[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=1[O:27][CH3:28])=[O:15])#[N:12].O>C(O)C.O.C(O)C>[OH:3][NH:2][N:12]=[CH:11][CH:13]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:14]([NH:16][C:17]1[C:22]([O:23][CH3:24])=[CH:21][C:20]([O:25][CH3:26])=[CH:19][C:18]=1[O:27][CH3:28])=[O:15]

Participants

7

Reactant 4

HCID 962Water2×HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochloride2×HCID 10496352alpha-Cyano-N-(2,4,6-trimethoxyphenyl)benzene acetamide

Product 1

HCID 70113100alpha-[(hydroxyamino)iminomethyl]-N-(2,4,6-trimethoxyphenyl)-benzeneacetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 19096565Water ethanolSolvent

Procedure

Hydroxylamine hydrochloride (11.95 g, 0.17 mol) was added to a solution of triethylamine (23.9 mL, 0.17 mol) in 50% ethanol/water (40 mL), and the mixture was stirred with ice, cooling until the NH2OH.HCl dissolved (0.5 hour). The mixture was then diluted with ethanol (300 mL) and α-cyano-N-(2,4,6-trimethoxyphenyl)-benzene acetamide (44.9 g, 0.138 mol) added in one portion and the mixture refluxed for 8 hours, allowed to cool, and poured into water (2 L) to yield a 2-phase oil/water mixture. The aqueous phase was concentrated in vacuo and the precipitate collected. The oil phase was triturated with chloroform to yield a white solid which was combined with the previous lot to yield 33.6 g, 68%, % (found): C, 60.35; H, 6.11; N, 11.60.

Workup

  1. dissolutiondissolved (0.5 hour)
  2. additionadded in one portion
  3. temperaturethe mixture refluxed for 8 hours
  4. temperatureto cool
  5. concentrationThe aqueous phase was concentrated in vacuo
  6. customthe precipitate collected
  7. customThe oil phase was triturated with chloroform
  8. customto yield a white solid which
  9. customto yield 33.6 g, 68%

Sources & evidence

ORD record
ord-10d19bb01cd94478a170ac42e79c04f1
Source dataset
uspto-grants-1997_12
Patent number
US05693657

Reaction notes

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