Methanol → HCID 86749498, compound

HRID 1379246Notes

Reaction equation

HRID 1379246 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([N+:30]([O-:32])=[O:31])=[C:13]([N:15]3[C:20](=[O:21])[NH:19][C:18](=[O:22])[N:17]([CH2:23][C:24]([O:26][CH2:27]C)=[O:25])[C:16]3=[O:29])[CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34].S(=O)(=O)(O)O.CO>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:10]=[CH:11][C:12]([N+:30]([O-:32])=[O:31])=[C:13]([N:15]3[C:20](=[O:21])[NH:19][C:18](=[O:22])[N:17]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:16]3=[O:29])[CH:14]=2)[CH:5]=[CH:4][C:3]=1[C:33]([F:35])([F:34])[F:36]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric Acid5×HCID 86749499HCID 86749499, compound

Product 1

HCID 86749498HCID 86749498, compound

Procedure

A solution of ethyl 3-{5-[(2-chloro-α,α,α-trifluoro-p-tolyl)oxy]-2-nitrophenyl}tetrahydro-2,4,6-trioxo-s-triazine-1(2H)-acetate (16.0 g, 0.030 mol) and sulfuric acid (1.60 mL, 0.030 mol) in methanol (240 mL, 5.92 mol) is refluxed overnight, treated with sulfuric acid (0.40 mL), refluxed for 90 minutes, treated with sulfuric acid (0.80 mL), refluxed for 90 minutes, treated with sulfuric acid (0.80 mL), refluxed for 1 hour, treated with sulfuric acid (0.80 mL), refluxed for 90 minutes, stirred at room temperature overnight, partially concentrated in vacuo and diluted with ether. The organic mixture is washed sequentially with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title product as a white solid, mp 166°-167° C.

Workup

  1. temperaturerefluxed for 90 minutes
  2. temperaturerefluxed for 90 minutes
  3. temperaturerefluxed for 1 hour
  4. temperaturerefluxed for 90 minutes
  5. concentrationpartially concentrated in vacuo
  6. additiondiluted with ether
  7. washThe organic mixture is washed sequentially with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e53395eae644b80b13e3411437e2d73
Source dataset
uspto-grants-1997_09
Patent number
US05670641

Reaction notes

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