Dimethylformamide → HCID 4625969, compound

HRID 1599836Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of ethyl 2-aminobenzoate (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, 1.6 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 3.32 g (65%) of the title compound as a white solid, mp 65°-66° C.: 1H NMR (DMSO-d6) δ11.08 (s, 1H), 8.25 (dd, J=7.6, J=0.8, 1H), 7.95 (dd, J=8.0, J=1.2, 1H), 7.63 (t, J=8.4, 1H), 7.25 (dt, J=7.6, J=1.2, 1H), 4.33 (q, J=7.2, 2H), 4.23 (s, 2H), 1.33 (t, J=7.2, 3H); 13C NMR (DMSO-d6) δ166.82, 165.02, 138.86, 133.95, 130.62, 123.93, 121.11, 118.23, 61.30, 30.40, 13.99; 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-e1d5447e7f0b4511803c5dc50e05ec42
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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