Dimethylformamide → HCID 18929235, compound

HRID 1599830Notes

Reaction equation

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

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of 4-fluoro-2-aminobenzoic acid (5.0 g, 32.2 mmol) in a mixture of anhydrous DMF (30 mL) and anhydrous dioxane (30 mL) in a 250 mL 3-necked round-bottomed flask which was equipped with a constant addition funnel (60 mL) was cooled with an ice-bath to -5° C. Bromoacetyl bromide (6.44 g, 2.8 mL, 32.2 mmol) was added dropwise while keeping the internal temperature between -5° and 0° C. over a 1/2 h period. After the addition of the bromoacetyl bromide was completed, the solution was warmed to room temperature and stirred overnight. To this solution was slowly added 150 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 8.13 g (91.4%) of the title compound as a white solid, mp 166°-168° C.: 1H NMR (DMSO-d6) δ13.92 (bs, 1H), 11.83 (s, 1H), 8.32 (dd, J=12, J=2.4, 1H), 8.09 (dd, J=9.2, J=6.8, 1H), 7.06 (ddd, J=8.8, J=9.2, J=2.4, 1H), 4.29 (s, 2H); 13C NMR (DMSO-d6) δ168.55, 165.60, 164.80 (d, J=248), 142.29 (d, J=12.9), 133.93 (d, J=10.6), 113.19, 110.42 (d, J=22), 106.43 (d, J=28), 30.54; MS (EI, m/z) 275 (M+).

Workup

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

Sources & evidence

ORD record: ord-1d71d1d675e14f7288e4896149259476
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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