Hydrochloric Acid → HCID 19760000, compound

HRID 1613859Notes

Reaction equation

HRID 1613859 reaction equation
[OH:1][C:2]1[CH:17]=[CH:16][C:5]2[N:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.C([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])C.[C:25](Cl)(=[O:32])[CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30].Cl>C1(C)C=CC=CC=1>[F:15][C:12]1[CH:11]=[CH:10][C:9]([C:7]2[O:8][C:4]3[CH:3]=[C:2]([O:1][C:25]([CH2:26][CH2:27][CH2:28][C:29]([O:8][C:4]4[CH:5]=[CH:24][C:23]5[N:20]=[C:21]([C:22]6[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=6)[O:1][C:2]=5[CH:3]=4)=[O:30])=[O:32])[CH:17]=[CH:16][C:5]=3[N:6]=2)=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 17887Pentanedioyl dichlorideHCID 19759988HCID 19759988, compound

Product 1

HCID 19760000HCID 19760000, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-Hydroxy-2-(p-fluorophenyl)benzoxazole (20.00 g, 0.087 mole) from Example 7 is mixed with 300 ml of toluene and 12 g (0.12 mole) of triethylamine under nitrogen atmosphere. Glutaryl chloride (7.10 g, 0.042 mole) is added and the mixture is stirred and heated at reflux for 5 hours. After cooling to room temperature 300 ml of 1N hydrogen chloride is added and stirring is continued for a few minutes. The resulting precipitate is filtered and recrystallized from DMF. The title compound (20.5 g, 88 percent yield), illustrated in Formula 16, is recovered and has a melting point of 189° C.-190° C. ##STR19##

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. additionis added
  4. stirringstirring
  5. waitis continued for a few minutes
  6. filtrationThe resulting precipitate is filtered
  7. customrecrystallized from DMF

Sources & evidence

ORD record
ord-1c71212e7fdd4e7db0f378060fc25cea
Source dataset
uspto-grants-1993_03
Patent number
US05194562

Reaction notes

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