Dimethylformamide → HCID 18929204, compound

HRID 1599838Notes

Reaction equation

[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.CN(C=O)C.[Br:16][CH2:17][C:18](Br)=[O:19]>O1CCOCC1>[Br:16][CH2:17][C:18]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1)=[O:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-aminobenzyl cyanide (7.5 g, 56.7 mmol) in a mixture of anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) in a 250 mL 3-necked round-bottomed flask equipped with a constant addition funnel (60 mL) was cooled to 0° C. using an ice-bath. Bromoacetyl bromide (11.4 g, 4.98 mL, 56.7 mmol) was added dropwise, keeping the internal temperature between 0° and 5° C. over a 1/2 h period. After the addition of the bromoacetyl bromide was completed, the solution was warmed to rt, stirred overnight, and then the solution was slowly poured into 500 mL of ice-water, causing a solid to precipitate. The precipitate was filtered, washed with water, and then dried in a vacuum dessicator overnight to afford 10.5 g (95%) of the title compound as a pale-orange solid, mp 127°-135° C. (decomp): 1H NMR (DMSO-d6) δ10.45 (s, 1H), 7.59 (d, J=9.2, 2H), 7.31 (d, J=9.2, 2H), 4.03 (s, 2H), 3.98 (s, 2H); 13C NMR (DMSO-d6) δ164.83, 137.98, 128.60, 126.42, 119.61, 119.26, 30.31, 21.81; MS (EI, m/z) 252 (M+).

Workup

customequipped with a constant addition funnel (60 mL)
customthe internal temperature between 0° and 5° C.
customover a 1/2 h
temperaturethe solution was warmed to rt
customto precipitate
filtrationThe precipitate was filtered
washwashed with water
customdried in a vacuum dessicator overnight

Sources & evidence

ORD record: ord-8ae070fdb92f4fc199d49a9ec72d0914
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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