Hydrogen Bromide → HCID 19905290, compound

HRID 2371864Notes

Reaction equation

HRID 2371864 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)=[O:3].Br.[S:12]1[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]1.[CH2:18]=O.Br>CC(C)=O.C(O)C>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][CH2:18][N:14]2[CH2:15][CH2:16][CH2:17][S:12][CH2:13]2)=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 712Formaldehyde2×HCID 98284'-FluoroacetophenoneHCID 21658587HCID 21658587, compound

Product 1

HCID 19905290HCID 19905290, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Conditions

Temperature
-5 °C

Procedure

A mixture containing 8.28 g (0.06 mol) of 4-fluoroacetophenone, 11.05 g (0.06 mol) of tetrahydro-1,3-thiazine hydrobromide, 2.70 g (0.09 mol) of paraformaldehyde, 25 ml ethanol and 0.1 ml of 48% hydrobromic acid is heated under reflux while stirring. After one hour an additional amount of 1.8 g (0.06 mol) of paraformaldehyde is portionwise added, the reaction mixture is heated for an additional 2 hours and then 80 ml of acetone are added. The mixture is cooled at -5° C. to give 12.73 g of product which is recrystallized from methanol to obtain 9.02 g (45.0%) of glistening crystalline hydrobromide of the title compound, m.p.: 210°-203° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux
  3. temperaturethe reaction mixture is heated for an additional 2 hours

Sources & evidence

ORD record
ord-df0d79064d4246f993c97a70bd58f762
Source dataset
uspto-grants-1992_03
Patent number
US05096902

Reaction notes

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