Bromide ion → Methyl 2-((Bromoacetyl)Amino)Benzoate(WX618077)

HRID 1599832Notes

Reaction equation

[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].CN(C=O)C.[Br:17][CH2:18][C:19](Br)=[O:20].[Br-]>O1CCOCC1>[Br:17][CH2:18][C:19]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([O:10][CH3:11])=[O:9])=[O:20]

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of methyl anthranilate (10.0 g, 66 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 -5° C. using an ice-bath. Bromoacetyl bromide (13.32 g, 5.8 mL, 66 mmol) was added dropwise, keeping the internal temperature between -5° to 0° C. over a 1/2 h period. After the addition of the bromide was completed, the solution was warmed to rt, stirred overnight and then the resulting solution was slowly poured into 500 mL of ice-water, causing a white solid to precipitate. The precipitate was filtered, washed with water, and then dried in a vacuum dessicator overnight to afford 16.4 g (91%) of the title compound as a white solid, mp 86°-87° C.: 1H NMR (DMSO-d6) δ11.07 (s, 1H), 8.24 (dd, J=8.4, J=1.2, 1H), 7.94 (dd, J=8.0, J=1.6, 1H), 7.64 (dt, J=8.8, J=1.6, 1H), 7.24 (dt, J=8.4, J=1.2, 1H), 4.23 (s, 2H), 3.87 (s, 3H); 13C NMR (DMSO-d6) δ167.26, 165.02, 138-82, 133.97, 130.62, 123.91, 121.13, 118-09, 52.46, 30.34; MS (EI, m/z) 271 (M+).

Workup

customequipped with a constant addition funnel (60 mL)
custombetween -5° to 0° 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-32d52f357cdc4b6882b591315e235b5c
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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