4-Nitrophenol → 2-Benzyl-5-methoxy-3-p-nitrophenoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

HRID 246834Notes

Reaction equation

HRID 246834 reaction equation
[CH2:1]([N:8]1[C:13](Cl)=[N:12][C:11]([O:15][CH3:16])=[N:10][S:9]1(=[O:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=[C:21]([OH:28])[CH:20]=1.N1C=CC=CC=1>C(Cl)Cl>[CH2:1]([N:8]1[C:13]([O:28][C:21]2[CH:20]=[CH:19][C:24]([N+:25]([O-:27])=[O:26])=[CH:23][CH:22]=2)=[N:12][C:11]([O:15][CH3:16])=[N:10][S:9]1(=[O:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 1049PyridineHCID 140505002-Benzyl-3-chloro-5-methoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

Product 1

HCID 140505012-Benzyl-5-methoxy-3-p-nitrophenoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2benzyl-3-chloro-5-methoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide (3.8 g) in methylene chloride (10 ml) is added dropwise to a stirred mixture of p-nitrophenol (1.7 g) and pyridine (2.4 g) in methylene chloride (20 ml). The reaction mixture is heated to reflux for 3 hours, cooled, washed with 3N aq. HCl and sat'd aq. Na2CO3. The methylene chloride layer is dried, filtered and evaporated in vacuo yielding the desired product as an oil.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 hours
  3. temperaturecooled
  4. washwashed with 3N aq. HCl
  5. dry with materialThe methylene chloride layer is dried
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ecd075c8c4a04529824437bb11f46b86
Source dataset
uspto-grants-1987_11
Patent number
US04704388

Reaction notes

Loading…