Dimethylformamide → HCID 23625045, compound

HRID 1599840Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.CN(C=O)C.[Br:22][CH2:23][C:24](Br)=[O:25]>O1CCOCC1>[Br:22][CH2:23][C:24]([NH:14][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][OH:8])=[CH:16][CH:15]=1)=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-(((tert-butyldimethylsilyl)oxy)methyl)aniline (14.0 g, 59 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 (11.91 g, 5.18 mL, 59 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. The resulting precipitate was filtered, washed with water, and then dried in a vacuum dessicator overnight to afford 8.73 g (61%) Of the title compound as a pale yellow crystals, mp 128°-134° C. (decomp), became wet at 89°-93° C.: 1H NMR (DMSO-d6) δ10.35 (s, 1H), 7.52 (d, J=8.8, 2H), 7.26 (d, J=8.8, 2H), 4.43 (s, 2H), 4.04 (s, 2H); 13C NMR (DMSO-d6) δ164.58, 138.00, 137.15, 126.97, 118.94, 62.51, 30.43; MS (El, m/z) 243 (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
filtrationThe resulting precipitate was filtered
washwashed with water
customdried in a vacuum dessicator overnight

Sources & evidence

ORD record: ord-e4fe3aaa73004bb2a345a450b128a6a8
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05741926

Reaction notes

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