Dimethylformamide → HCID 18929253, compound

HRID 1599839Notes

Reaction equation

[CH2:1]([O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].C[N:14](C=O)C.[Br:18][CH2:19][C:20](Br)=[O:21]>O1CCOCC1>[Br:18][CH2:19][C:20]([NH:10][C:9]1[CH:8]=[CH:7][C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])([NH2:14])[CH2:12][CH:11]=1)=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-butoxyaniline (3.0 g, 18 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 (3.68 g, 1.60 mL, 18 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 3.38 g (65%) of the title compound as a pale purple solid, mp 131°-134° C.: 1H NMR (DMSO-d6) δ10.23 (s, 1H), 7.45 (d, J=8.8, 2H), 6.88 (d, J=9.2, 2H), 3.99 (s, 2H), 3.92 (t, J=6.4, 2H), 1.68-1.65 (m, 2H), 1.42-1.40 (m, 2H), 0.92 (t, J=7.2, 3H); 13C NMR (DMSO-d6) δ164.18, 155.01, 131.57, 120.70, 114.50, 67.22, 30.73, 30.38, 18.70, 13.66; MS (EI, m/z) 287 (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-0813bfa46b824bc0a1cc3c6e78d8fb26
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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