O-Methylhydroxylamine hydrochloride → (Z)-N-methoxy-1-(2-phenyl-1,3-thiazol-4-yl)-1-(3,4,5-trimethoxyphenyl)methanimine

HRID 70033Notes

Reaction equation

HRID 70033 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[C:10]([C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[CH3:27][O:28][NH2:29]>N1C=CC=CC=1>[CH3:27][O:28]/[N:29]=[C:12](\[C:10]1[N:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[S:8][CH:9]=1)/[C:14]1[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=1

Participants

4

Reactant 2

HCID 521874O-Methylhydroxylamine hydrochlorideHCID 252274304-(3,4,5-Trimethoxybenzoyl)-2-phenylthiazole

Product 1

HCID 53364196(Z)-N-methoxy-1-(2-phenyl-1,3-thiazol-4-yl)-1-(3,4,5-trimethoxyphenyl)methanimine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 1h (110 mg, 0.59 mmol) in 10 mL pyridine was added O-methylhydroxylamine hydrochloride (52 mg, 0.63 mmol) and the mixture was stirred at 60° C. for overnight. The reaction was quenched with 1 N HCl solution, extracted with ethyl acetate and dried with MgSO4. The solvent was removed under reduced pressure to yield a crude product, which was purified by column chromatography to give pure compounds 2f-cis (41 mg) and 2f-trans (33 mg). 1H NMR (500 MHz, CDCl3) δ 8.13 (s, 1H), 7.96-7.94 (m, 2H), 7.45-7.44 (m, 3H), 6.94 (s, 2H), 4.13 (s, 3H), 3.91 (s, 6H), 3.88 (s, 3H). MS (ESI) m/z 407.2 (M+Na)+.

Workup

  1. customThe reaction was quenched with 1 N HCl solution
  2. extractionextracted with ethyl acetate
  3. dry with materialdried with MgSO4
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-37835176ab6544849cb7b1b9aaf73fe4
Source dataset
uspto-grants-2014_09
Patent number
US08822513B2

Reaction notes

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