Triethylamine → N-Methoxy-N,3-dimethylbut-2-enamide

HRID 1975077Notes

Reaction equation

[CH3:1][C:2]([CH3:7])=[CH:3][C:4](Cl)=[O:5].Cl.[CH3:9][NH:10][O:11][CH3:12].C(N(CC)CC)C>ClCCl>[CH3:12][O:11][N:10]([CH3:9])[C:4](=[O:5])[CH:3]=[C:2]([CH3:7])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

3,3-Dimethylacryloyl chloride (28.2 mL, 0.253 mol) was slowly added to a mixture of N,O-dimethylhydroxylamine hydrochloride (27.2 g, 0.278 mol) and triethylamine (75 mL, 0.519 mol) in dichloromethane (300 mL) at 0° to 30° C. and stirred 1 h at 0° C. The resultant mixture was washed with 1 N hydrochloric acid and then with 1 N sodium hydroxide and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue vacuum distilled (60° to 70° C. at 0.2 mm Hg) to give the product, 26.8 g (74%) as a colorless oil; IR(neat): 2938 and 1660 cm-1 : MS: m/z 144 (MH+); 1H NMR(CDCl3): δ 1.91 (d, J=1.2 Hz, 3H), 2.14 (d, J=0.9 Hz, 3H), 3.20 (s, 3H), 3.68 (s, 3H), and 6.12 (bs, 1H).

Workup

washThe resultant mixture was washed with 1 N hydrochloric acid
dry with materialwith 1 N sodium hydroxide and dried over magnesium sulfate
customThe solvent was evaporated in vacuo
distillationthe residue vacuum distilled (60° to 70° C. at 0.2 mm Hg)
customto give the product, 26.8 g (74%) as a colorless oil

Sources & evidence

ORD record: ord-3e0087a308104fbab78ada9717d1e44c
Source dataset: uspto-grants-1994_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05284857

Reaction notes

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