Hexamethylenetetramine → HCID 22339565, compound

HRID 585144Notes

Reaction equation

HRID 585144 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:18]2[C:23](=[O:24])[NH:22][C:21](=[O:25])[CH:20]=[N:19]2)[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:38](O)=[O:39]>>[Cl:1][C:2]1[CH:3]=[C:4]([N:18]2[C:23](=[O:24])[NH:22][C:21](=[O:25])[CH:20]=[N:19]2)[CH:5]=[C:6]([Cl:17])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:38]=[O:39])[CH:10]=1

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 22339608HCID 22339608, compound

Product 1

HCID 22339565HCID 22339565, compound

Procedure

A solution of 2-[3,5-dichloro-4-(4-methoxy-phenoxy)-phenyl]-2H-[1,2,4]triazine-3,5-dione (1 g) and hexamethylenetetraamine (0.6 g) in trifluoroacetic acid (8 mL) was stirred at 70° C. for 18 h. The trifluoroacetic acid was removed in vacuo, water added and the resulting mixture was stirred for 30 min. The residue was extracted with ethyl acetate, the organic phase washed with water, brine, dried (Na2SO4), concentrated in vacuo and flash chromatographed on silica gel (35% acetone/hexanes) to afford the title compound of Step A as an off-white solid, 1.0 g (m.p. 184-187° C.).

Workup

  1. customThe trifluoroacetic acid was removed in vacuo, water
  2. additionadded
  3. extractionThe residue was extracted with ethyl acetate
  4. washthe organic phase washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo and flash
  7. customchromatographed on silica gel (35% acetone/hexanes)

Sources & evidence

ORD record
ord-32c9a941632f43e4ba1f17bab249842a
Source dataset
uspto-grants-2005_08
Patent number
US06930107B2

Reaction notes

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