Triethylamine → HCID 136395918, compound

HRID 1378449Notes

Reaction equation

HRID 1378449 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:20]#[N:21])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19].Cl.[NH2:23][OH:24].C(N(CC)CC)C>CO>[CH3:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][CH2:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4](=[N:3][O:2][CH3:1])[C:20](=[N:23][OH:24])[NH2:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 54046985HCID 54046985, compound

Product 1

HCID 136395918HCID 136395918, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of part of the sample of isomer 1 of 2-(2-methylphenoxymethyl) benzoyl cyanide O-methyloxime (280 mg), hydroxylamine hydrochloride (80 mg) and triethylamine (110 mg) in methanol (5 ml) was heated under reflux for 5 hours. The reaction mixture was concentrated and the residue, dissolved in ethyl acetate, was washed with water, dried, concentrated, and chromatographed using ethyl acetate:hexane (1:1) as eluant to give two stereoisomers of 2-[2-(2-methylphenoxymethyl)phenyl]-2-methoxyimino acetamide oxime. Isomer I (200 mg, 67% yield), eluted first, was a white solid, mp 140° C., 1H NMR (CDCl3): δ 2.3 (3H,s), 4.0 (3H,s) and 5.05 (2H,s) ppm. Isomer II (100 mg, 33% yield), was also a white solid, mp 110°-2° C., 1H NMR (CDCl3): δ 2.3 (3H,s), 4.0 (3H,s) and 5.2 (2H,s) ppm.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe residue, dissolved in ethyl acetate
  5. washwas washed with water
  6. customdried
  7. concentrationconcentrated
  8. customchromatographed

Sources & evidence

ORD record
ord-1fdd601d1f954da5a2893c53e2752339
Source dataset
uspto-grants-1997_09
Patent number
US05668160

Reaction notes

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