Triethylsilane → N-[5-Chloro-4-(2-chloro-ethyl)-2-methyl-phenyl]-acetamide

HRID 2211907

Reaction equation

[Cl:1][C:2]1[C:3]([C:13](=O)[CH2:14][Cl:15])=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([CH2:13][CH2:14][Cl:15])=[CH:4][C:5]([CH3:12])=[C:6]([NH:8][C:9](=[O:11])[CH3:10])[CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-[5-Chloro-4-(2-chloro-acetyl)-2-methyl-phenyl]-acetamide (10 g, 38.44 mmol) in trifluoroacetic acid (100 mL) at <20° C. was added portionwise, triethylsilane (15.35 mL, 96.1 mmol). The reaction was heated to 60° C. and stirred overnight. The reaction was cooled to rt and poured over ice/H2O and stirred for 30 min as a grey precipitate formed. The precipitate was collected by filtration and dried in vacuo overnight to give desired product (8.35 g, 33.92 mmol). Yield=88%; MS (APCI): 246 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 7.89 (s, 1H), 7.05 (s, 1H), 6.93 (bs, 1H, NH), 3.69 (t, J=7.26 Hz, 2H), 3.10 (t, J=7.26 Hz, 2H), 2.20 (d, J=4.48 Hz, 3H).

Workup

temperatureThe reaction was cooled to rt
stirringstirred for 30 min as a grey precipitate
customformed
filtrationThe precipitate was collected by filtration
customdried in vacuo overnight

Sources & evidence

ORD record: ord-731ee461f91146d2852063712cd16c60
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101886B2

Linked notes

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