Dimethylformamide → HCID 586678, compound

HRID 1599837Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-nitroaniline (10.0 g, 72.4 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 (14.60 g, 6.35 mL, 72.4 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 16.92 g (90%) of the title compound as a greenish yellow solid, mp 175°-178° C.: 1H NMR (DMSO-d6) δ10.98 (s, 1H), 8.24 (d, J=9.2, 2H), 7.83 (d, J=9.2, 2H), 4.10 (s, 2H); 13C NMR (DMSO-d6) δ165.77, 144.67, 142.62, 125.05, 119.01, 30.15; MS (EI, m/z) 285 (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-f847391f5205402ca410bcda929423f0
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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