4-Nitrophenol → 3-Amino-2-Benzyl-5-Methoxy-2H-1,2,4,6-thiatriazine-1,1-dioxide

HRID 1252028Notes

Reaction equation

HRID 1252028 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.C1C([N+:25]([O-])=O)=CC=C(O)C=1.N1C=CC=CC=1>C(Cl)Cl>[NH2:25][C:13]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[S:9](=[O:18])(=[O:17])[N:10]=[C:11]([O:15][CH3:16])[N:12]=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 201409183-Amino-2-Benzyl-5-Methoxy-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 aqueous HCl and saturated aqueous Na2CO3. The methylene chloride layer is dried over MgSO4, 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 aqueous HCl and saturated aqueous Na2CO3
  5. dry with materialThe methylene chloride layer is dried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-999073d452414398aaab29d980b94040
Source dataset
uspto-grants-1988_05
Patent number
US04742055

Reaction notes

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