Sodium Hydroxide → HCID 74042289, compound

HRID 2051778Notes

Reaction equation

HRID 2051778 reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[CH3:6][N:7]([C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=1[C:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)C=O>C(O)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([NH:7][CH3:6])=[C:11]([CH:12]=1)[C:17](=[N:4][OH:1])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 20378192HCID 20378192, compound

Product 1

HCID 74042289HCID 74042289, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4.0 g (0.1 mole) of powdered sodium hydroxide, 13.9 g (0.2 mole) of hydroxylamine hydrochloride, and 27.4 g (0.1 mole) of N-methyl-N-(2-benzoyl-4-chlorophenyl)formamide in 200 ml of ethanol was refluxed for 3 days. About one-half of the ethanol was distilled off and the reaction mixture was poured into 500 ml of water and then extracted with three 100-ml portions of methylene chloride. The extracts were combined, washed with water, dried (MgSO4) and evaporated to dryness under reduced pressure to give 26 g (100%) of a light yellow glass: 1H nmr (DMSO-d6) partial: δ 2.74 ppm (d, J=5 Hz) and δ 2.94 ppm (d, J=5) for CH3 split by NH; δ 11.26 ppm (45% ) and 11.53 ppm (55%) for =NOH (on addition of D2O, the splitting of the methyl peaks is lost).

Workup

  1. temperaturewas refluxed for 3 days
  2. distillationAbout one-half of the ethanol was distilled off
  3. additionthe reaction mixture was poured into 500 ml of water
  4. extractionextracted with three 100-ml portions of methylene chloride
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-16b9479ddb3e4f6e8cc51c5a2f417913
Source dataset
uspto-grants-1980_01
Patent number
US04182760

Reaction notes

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