Phosphorus tribromide → 8-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide

HRID 572747Notes

Reaction equation

[Br:1]P(Br)Br.O[CH:6]([C:8]1[CH:9]=[C:10]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[CH:14][C:13]2=[O:24])[CH3:7]>C(Cl)Cl>[BrH:1].[Br:1][CH:6]([C:8]1[CH:9]=[C:10]([C:25]([N:27]([CH3:29])[CH3:28])=[O:26])[CH:11]=[C:12]2[C:17]=1[O:16][C:15]([N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)=[CH:14][C:13]2=[O:24])[CH3:7]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of tribromophosphine 1M in CH2Cl2 (0.346 mL, 0.35 mmol) at 25° C., was added dropwise to 8-(1-hydroxyethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide (120 mg, 0.35 mmol) suspended in DCM (1 mL). The resulting suspension was stirred at 25° C. for 4 days. The resulting gum was triturated in ether to give a precipitate which was collected by filtration, washed with ether and dried to a constant weight to afford 8-(1-bromoethyl)-N,N-dimethyl-2-morpholino-4-oxo-4H-chromene-6-carboxamide hydrobromide (140 mg, 82%) as a white solid, which was used without further purification. Mass Spectrum: M+H+ 409.

Workup

customThe resulting gum was triturated in ether
customto give a precipitate which
filtrationwas collected by filtration
washwashed with ether
customdried to a constant weight

Sources & evidence

ORD record: ord-fa351d891eca4e06a973bcc863b3f870
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029374B2

Reaction notes

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