O-Xylene → 2-(2-Fluorophenyl)thiazolo[5,4-b]pyridine

HRID 259565Notes

Reaction equation

HRID 259565 reaction equation
[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][C:7]1[C:8](=O)[NH:9][CH:10]=[CH:11][CH:12]=1)=O.C1(C)C(C)=CC=CC=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27]>N1C=CC=CC=1>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]1[S:27][C:8]2[C:7]([N:6]=1)=[CH:12][CH:11]=[CH:10][N:9]=2

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 14817Phosphorus sulfide (P2S5)HCID 124613983-(2-Fluorobenzoylamino)-2-pyridone

Product 1

HCID 227547712-(2-Fluorophenyl)thiazolo[5,4-b]pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(2-Fluorobenzoylamino)-2-pyridone (2 g.), 60 ml. of xylene and 15 ml of pyridine were heated until solution was complete. To this solution was added 6.5 grams of phosphorus pentasulfide and the mixture was heated at reflux for 16 hours. The reaction mixture was decanted from a gummy residue while hot, and the solvents were concentrated to dryness. The crystalline residue was recrystallized from ethanol to give 2-(2-fluorophenyl)thiazolo[ 5,4-b]pyridine, m.p. 119°-121° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe reaction mixture was decanted from a gummy residue while hot, and the solvents
  4. concentrationwere concentrated to dryness
  5. customThe crystalline residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-f46c679bcfa345cb8ce39092c9cc91f3
Source dataset
uspto-grants-1977_07
Patent number
US04038396

Reaction notes

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