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4-Nitrophenol → 2-Cyclohexyl-5-methoxy-3-para-nitrophenoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

HRID 246840
Notes
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Reaction equation

HRID 246840 reaction equation
Cl[C:2]1[N:3]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[S:4](=[O:11])(=[O:10])[N:5]=[C:6]([O:8][CH3:9])[N:7]=1.[N+:18]([C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)([O-:20])=[O:19].N1C=CC=CC=1>C(Cl)Cl.C1COCC1.C>[CH:12]1([N:3]2[C:2]([O:27][C:24]3[CH:25]=[CH:26][C:21]([N+:18]([O-:20])=[O:19])=[CH:22][CH:23]=3)=[N:7][C:6]([O:8][CH3:9])=[N:5][S:4]2(=[O:11])=[O:10])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 9804-NitrophenolHCID 1049PyridineHCID 129179853-Chloro-2-cyclohexyl-5-methoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

Product 1

HCID 212691072-Cyclohexyl-5-methoxy-3-para-nitrophenoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

Reagents, catalysts & solvents 3

HCID 297MethaneSolvent
HCID 6344
Dichloromethane
Solvent
2×
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the chlorothiatriazine obtained in Step 3. above (92.3 g) in methylene chloride (250 ml) is added dropwise to a stirred solution of para-nitrophenol (49.4 g) and pyridine (70.2 g) in methylene chloride (500 ml) and refluxed for 3 hours. The reaction mixture is washed with 3N HCl and sodium bicarbonate solution. The methylene chloride layer is dried, filtered, washed and evaporated yielding a solid which is dissolved in hot THF with charcoal, filtered and evaporated. The resulting solid is washed with diethyl ether, dissolved in methylene chloride, filtered through silica gel, washed with methylene chloride, filtered through Celite®, evaporated, and triturated with diethyl ether affording a yellow solid. The solid is recrystallized from hot THF, yielding the desired product as a solid used in the next step without further purification.

Workup

  1. temperaturerefluxed for 3 hours
  2. washThe reaction mixture is washed with 3N HCl and sodium bicarbonate solution
  3. dry with materialThe methylene chloride layer is dried
  4. filtrationfiltered
  5. washwashed
  6. customevaporated
  7. customyielding a solid which
  8. filtrationfiltered
  9. customevaporated
  10. washThe resulting solid is washed with diethyl ether
  11. dissolutiondissolved in methylene chloride
  12. filtrationfiltered through silica gel
  13. washwashed with methylene chloride
  14. filtrationfiltered through Celite®
  15. customevaporated
  16. customtriturated with diethyl ether affording a yellow solid
  17. customThe solid is recrystallized from hot THF

Sources & evidence

ORD record
ord-f8ffcad9998e44deaccca8964f30c935
Source dataset
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04704388

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes