p-Fluoronitrobenzene → 4-(4-Nitrophenyl)thiomorpholine

HRID 235619Notes

Reaction equation

HRID 235619 reaction equation
[NH:1]1[CH2:6][CH2:5][S:4][CH2:3][CH2:2]1.F[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1>>[N+:14]([C:11]1[CH:12]=[CH:13][C:8]([N:1]2[CH2:6][CH2:5][S:4][CH2:3][CH2:2]2)=[CH:9][CH:10]=1)([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 67164Thiomorpholine

Product 1

HCID 31247254-(4-Nitrophenyl)thiomorpholine

Procedure

(ab) 23 ml of thiomorpholine are slowly added dropwise at about 80° to 17.17 g of p-fluoronitrobenzene in such a manner that the internal temperature does not rise above 110°. The mixture is then stirred at 120° for an additional 1 hour, whereupon it is extracted three times with 1 l of dichloromethane each time and the organic phases are washed three times with 500 ml of water each time, dried over sodium sulfate and evaporated. By recrystallization of the crude product from dichloromethane/ether, there is obtained 4-(p-nitrophenyl)-tetrahydro-4-H-1,4-thiazine of melting point 142°-144°.

Workup

  1. customdoes not rise above 110°
  2. extractionis extracted three times with 1 l of dichloromethane each time
  3. washthe organic phases are washed three times with 500 ml of water each time
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customBy recrystallization of the crude product from dichloromethane/ether

Sources & evidence

ORD record
ord-22830927e041493285e77d80e2818c24
Source dataset
uspto-grants-1987_02
Patent number
US04640918

Reaction notes

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