Hydrogen Bromide → 2-(7-Bromomethyl-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one

HRID 1988574Notes

Reaction equation

HRID 1988574 reaction equation
O[CH2:2][C:3]1[CH:16]=[C:15]2[C:6]([S:7][C:8]3[C:9]([C:17]4[O:18][C:19]([N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH2:25]5)=[CH:20][C:21](=[O:23])[CH:22]=4)=[CH:10][CH:11]=[CH:12][C:13]=3[CH2:14]2)=[CH:5][CH:4]=1.[BrH:30]>C(Cl)(Cl)Cl>[Br:30][CH2:2][C:3]1[CH:16]=[C:15]2[C:6]([S:7][C:8]3[C:9]([C:17]4[O:18][C:19]([N:24]5[CH2:29][CH2:28][O:27][CH2:26][CH2:25]5)=[CH:20][C:21](=[O:23])[CH:22]=4)=[CH:10][CH:11]=[CH:12][C:13]=3[CH2:14]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 58687907HCID 58687907, compound

Product 1

HCID 115328922-(7-Bromomethyl-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 2-(7-Hydroxymethyl-9H-thioxanthen-4-yl)-6-morpholin-4-yl-pyran-4-one (3)(240 mg, 0.59 mmol) in chloroform (10 mL) was saturated with hydrogen bromide by bubbling hydrogen bromide gas through the reaction mixture until the solution became cloudy. After 18 hours, hydrogen bromide gas was again bubbled through the reaction mixture. The reaction mixture was washed with saturated NaHCO3 and water. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The brown coloured solid was dried under vacuum at 50° C. to give the crude title compound (assumed 100%) which was used without any further purification. m/z (LC-MS, ESP): 470.2 [M+H]+ (1:1, bromine isotope ratio present), R/T=3.86 mins

Workup

  1. customby bubbling hydrogen bromide gas through the reaction mixture until the solution
  2. customhydrogen bromide gas was again bubbled through the reaction mixture
  3. washThe reaction mixture was washed with saturated NaHCO3 and water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe brown coloured solid was dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-bc6a5cbb99334c8392b3625a68b41314
Source dataset
uspto-grants-2010_01
Patent number
US07642254B2

Reaction notes

Loading…