4-Nitrophenol → HCID 12785931, compound

HRID 246835Notes

Reaction equation

HRID 246835 reaction equation
Cl[C:2]1[N:3]([CH3:12])[S:4](=[O:11])(=[O:10])[N:5]=[C:6]([O:8][CH3:9])[N:7]=1.[CH:13]1[C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=[C:15]([OH:22])[CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:9][O:8][C:6]1[N:7]=[C:2]([O:22][C:15]2[CH:14]=[CH:13][C:18]([N+:19]([O-:21])=[O:20])=[CH:17][CH:16]=2)[N:3]([CH3:12])[S:4](=[O:11])(=[O:10])[N:5]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 1571952H-1,2,4,6-Thiatriazine, 3-chloro-5-methoxy-2-methyl-, 1,1-dioxide

Product 1

HCID 12785931HCID 12785931, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-chloro-5-methoxy-2-methyl-2H-1,2,4,6-thiatriazine-1,1-dioxide (48 g) in methylene chloride (25.5 ml) is added dropwise to a stirred mixture of p-nitrophenol (38 g) and triethylamine (55 g) in methylene chloride (1 l). The mixture is stirred at RT for about 12 hours, refluxed for about 31/2 hours, concentrated in vacuo, the residue is treated with sat'd aq. Na2CO3 solution, and the resulting insoluble solid filtered and washed with water and CH2Cl2. The solid is recrystallized from ethyl acetate/acetonitrile yielding the p-nitrophenoxy compound as a crystalline solid, M.P.=220°-221° C.

Workup

  1. temperaturerefluxed for about 31/2 hours
  2. concentrationconcentrated in vacuo
  3. additionthe residue is treated with sat'd aq. Na2CO3 solution
  4. filtrationthe resulting insoluble solid filtered
  5. washwashed with water and CH2Cl2
  6. customThe solid is recrystallized from ethyl acetate/acetonitrile yielding the p-nitrophenoxy compound as a crystalline solid, M.P.=220°-221° C.

Sources & evidence

ORD record
ord-3e60619dfd9947ed98500303b05d6311
Source dataset
uspto-grants-1987_11
Patent number
US04704388

Reaction notes

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