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

HRID 1982169Notes

Reaction equation

HRID 1982169 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 2-benzyl-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-d15c02b1942f4f289167691268e6a8f7
Source dataset
uspto-grants-1986_06
Patent number
US04595683

Reaction notes

Loading…