Butyl bromide → HCID 12767208, compound

HRID 904138Notes

Reaction equation

[C:1](=[C:4]1[NH:8][C:7](=[O:9])[NH:6][C:5]1=[O:10])([CH3:3])[CH3:2].[H-].[Na+].[CH2:13](Br)[CH2:14][CH2:15][CH3:16]>CN(C)C=O>[CH2:13]([N:6]1[C:5](=[O:10])[C:4](=[C:1]([CH3:3])[CH3:2])[NH:8][C:7]1=[O:9])[CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 50 °C

Procedure

5-Isopropylidenehydantoin (5.6 g 0.04 mole) Journal of the Chemical Society, 2265 (1955) was added to a stirred suspension of sodium hydride (2.0 g 50% dispersion-oil removed by washing with light petroleum) in dry dimethylformamide (50 ml) and the mixture then heated at 50° C. for 15 minutes after which time a cream coloured solid separated. The mixture was cooled to room-temperature, a solution of n-butyl bromide (6.0 g 0.044 mole) in dry dimethylformamide (25 ml) added and the mixture heated at 80° C. for 4 hours. The mixture was cooled to room temperature and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was dissolved in water (200 ml) and extracted with ether (3×50 ml). The ethereal solution was dried (MgSO4) and the solvent removed to yield a solid (6.6 g) which was crystallised from light petroleum (b.p. 60°-80° C.) to yield the title compound as needles, m.p. 130° C. Yield=4.3 g=55%.

Workup

customseparated
temperatureThe mixture was cooled to room-temperature
temperaturethe mixture heated at 80° C. for 4 hours
temperatureThe mixture was cooled to room temperature
customevaporated to dryness in a rotary evaporator under reduced pressure
dissolutionThe residue was dissolved in water (200 ml)
extractionextracted with ether (3×50 ml)
dry with materialThe ethereal solution was dried (MgSO4)
customthe solvent removed

Sources & evidence

ORD record: ord-5e9a3e38ca91466790370bbd2b27811d
Source dataset: uspto-grants-1980_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04230709

Reaction notes

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