Pyridine → HCID 135817469, compound

HRID 1358524Notes

Reaction equation

HRID 1358524 reaction equation
[F:1][C:2]1[CH:10]=[C:6]([C:7]([NH2:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[F:12][C:13]1[CH:21]=[C:17]([C:18](O)=O)[C:16]([OH:22])=[CH:15][CH:14]=1.N1C=CC=CC=1.S(Cl)(Cl)=O>C1(C)C(C)=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:11][C:18]([C:17]3[CH:21]=[C:13]([F:12])[CH:14]=[CH:15][C:16]=3[OH:22])=[N:9][C:7](=[O:8])[C:6]=2[CH:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 676585-Fluorosalicylic acidHCID 137262825-Fluoro-2-hydroxybenzamide

Product 1

HCID 135817469HCID 135817469, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4.3 g of 5-fluoro-salicylamide and 4.7 g of 5-fluorosalicylic acid are boiled under reflux in 50 ml of xylene after addition of 0.3 ml of pyridine. 4.4 ml of thionyl chloride are added in the course of 2 h, the mixture is stirred for a further 1 h and the solvent is then distilled off under reduced pressure. The residue is suspended in 30 ml of ethanol, filtered off and washed with ethanol. After drying, 6-fluoro-2-(5-fluoro-2-hydroxyphenyl)benz[e][1,3]oxazin-4-one is obtained as slightly yellow crystals of m.p. 250-252 C.

Workup

  1. distillationthe solvent is then distilled off under reduced pressure
  2. filtrationfiltered off
  3. washwashed with ethanol
  4. customAfter drying

Sources & evidence

ORD record
ord-b67b352ef8ef411ea87d7de68fee6c9f
Source dataset
uspto-grants-2003_07
Patent number
US06596750B2

Reaction notes

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