Diphenyl Ether → HCID 13937025, compound

HRID 979523Notes

Reaction equation

HRID 979523 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH:12]=[C:13]1[NH:17][C:16](=[S:18])[NH:15][C:14]1=O.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:5]=[CH:4][C:3]2[CH:12]=[C:13]3[NH:17][C:16](=[S:18])[NH:15][C:14]3=[N:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 7583Diphenyl EtherHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 54279295HCID 54279295, compound

Product 1

HCID 13937025HCID 13937025, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 5-[[2-amino-4-(trifluoromethyl)phenyl]methylene]-2-thioxo-4-imidazolidinone (3.63 g, 12 mmol), pyridinium tosylate (1.8 g), and diphenyl ether (5.4 g) was heated at 180° C. under an atmosphere of argon. After 18 minutes, the mixture was cooled, chloroform (60 mL) added and the mixture refluxed. After 30 minutes the solid was filtered off and dissolved in a mixture of water (80 mL) and 10% sodium hydroxide solution (5 mL) with warming. Addition of acetic acid afforded a heavy precipitate which was filtered off, washed with water and dried in vacuo to give 1,3-dihydro-6-(trifluoromethyl)-2H-imidazo[4,5-b]quinolin-2-thione (1.79 g, 52%), m.p. >320° C.

Workup

  1. temperaturethe mixture was cooled
  2. temperaturethe mixture refluxed
  3. filtrationAfter 30 minutes the solid was filtered off
  4. dissolutiondissolved in a mixture of water (80 mL) and 10% sodium hydroxide solution (5 mL)
  5. temperaturewith warming
  6. additionAddition of acetic acid
  7. customafforded a heavy precipitate which
  8. filtrationwas filtered off
  9. washwashed with water
  10. customdried in vacuo

Sources & evidence

ORD record
ord-a26f5030271f4c71b4b4f965e3a0176c
Source dataset
uspto-grants-1987_05
Patent number
US04668686

Reaction notes

Loading…