Hydrogen Bromide → HCID 18470133, compound

HRID 2228906Notes

Reaction equation

HRID 2228906 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]O)=[O:7])=[CH:4][CH:3]=1.O.C(OCC)C.[BrH:24]>>[Br:24][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][NH:8][C:6](=[O:7])[C:5]1[CH:16]=[CH:17][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 3283Diethyl EtherHCID 18470387HCID 18470387, compound

Product 1

HCID 18470133HCID 18470133, compound

Procedure

6-(4-Chlorobenzoylamino)hexan-1-ol (17.0 g) was refluxed in 48% hydrobromic acid (260 ml) for 2.5 h. The mixture was cooled and added to water (450 ml) and diethyl ether (450 ml). The organic layer was washed with saturated sodium bicarbonate (450 ml) and brine (450 ml) and was dried over magnesium sulfate. Evaporation followed by recrystallisation from diethyl ether gave 1-bromo-6-(4-chlorobenzoylamino)hexane (8.6 g). 1H-NMR (CDCl3) δ 1.3-2.0 (8H, m), 3.35-3.55 (4H, m), 6.15 (1H, bs), 7.40 (2H, m) and 7.70 (2H, m).

Workup

  1. temperatureThe mixture was cooled
  2. washThe organic layer was washed with saturated sodium bicarbonate (450 ml) and brine (450 ml)
  3. dry with materialwas dried over magnesium sulfate
  4. customEvaporation
  5. customfollowed by recrystallisation from diethyl ether

Sources & evidence

ORD record
ord-155d6cd01d6041b38071a79445f55348
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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