4-Fluorothiophenol → HCID 23462885, compound

HRID 2286406Notes

Reaction equation

HRID 2286406 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.Br.[CH3:10][N:11]1[CH2:17][CH2:16][C:15]2=[CH:18][C:19](=[O:23])[C:20](=[O:22])[CH:21]=[C:14]2[CH2:13][CH2:12]1>CO>[OH:23][C:19]1[C:20]([OH:22])=[CH:21][C:14]2[CH2:13][CH2:12][N:11]([CH3:10])[CH2:17][CH2:16][C:15]=2[C:18]=1[S:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 677894-FluorothiophenolHCID 12668031HCID 12668031, compound

Product 1

HCID 23462885HCID 23462885, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.0 g. (0.0078 mole) of p-fluorothiophenol in 200 ml. of methanol was added portionwise 2 g. (0.0073 mole) of 3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine-7,8-dione hydrobromide (prepared as in Example 2) and the resulting mixture was stirred at room temperature under argon for 1 hour. The methanol was distilled from the reaction mixture in vacuo and the residue was partitioned between ether and water. The aqueous layer was extracted with ether and then made basic with ammonium hydroxide solution. The precipitate was filtered and the dried filtrate was chromatographed on silica using methanol/chloroform. The material eluted from the column was slurried with ether and filtered. Distillation of the ether gave 7,8-dihydroxy-6-(p-fluorophenylthio)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 164°-166° C.

Workup

  1. distillationThe methanol was distilled from the reaction mixture in vacuo
  2. customthe residue was partitioned between ether and water
  3. extractionThe aqueous layer was extracted with ether
  4. filtrationThe precipitate was filtered
  5. customthe dried filtrate was chromatographed on silica
  6. washThe material eluted from the column
  7. filtrationfiltered
  8. distillationDistillation of the ether

Sources & evidence

ORD record
ord-6ecba91589b74ad589616d81ef7f8f78
Source dataset
uspto-grants-1981_05
Patent number
US04265890

Reaction notes

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