Hexamethylenetetramine → HCID 54072969, compound

HRID 543382Notes

Reaction equation

HRID 543382 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([S:12]([N:15]=[CH:16][N:17]([CH3:19])[CH3:18])(=[O:14])=[O:13])[CH:6]=1)([CH3:4])[CH3:3].C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:32](O)=[O:33]>>[CH:32]([C:9]1[CH:10]=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH:6]=[C:7]([S:12]([N:15]=[CH:16][N:17]([CH3:19])[CH3:18])(=[O:13])=[O:14])[C:8]=1[OH:11])=[O:33]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 541555634-(1,1-Dimethylethyl)-2-dimethylaminomethyleneaminosulfonylphenol

Product 1

HCID 54072969HCID 54072969, compound

Procedure

2.84 g (0.01 mol) of 4-(1,1-dimethylethyl)-2-dimethylaminomethyleneaminosulfonylphenol are boiled under reflux with 1.4 g of urotropine in 10 ml of trifluoroacetic acid for 6 h. The mixture is poured onto ice-water, and the rubber-like mass which has separated out is taken up in ether, the solution is washed to neutrality and the solvent is removed in vacuo. The residue is chromatographed on silica gel using ethyl acetate/toluene 4:1 as the eluting agent. 2-formyl-4-(1,1-dimethylethyl)-6-dimethylaminomethyleneaminosulfonylphenol of melting point 182°-183° C. is obtained, and this is immediately dissolved in 2N sodium hydroxide solution. The solution is left on a steam bath for 30 minutes, and then the solution is acidified to pH 2-3 with 2N hydrochloric acid, and filtered with suction.

Workup

  1. additionThe mixture is poured onto ice-water
  2. customthe rubber-like mass which has separated out
  3. washthe solution is washed to neutrality
  4. customthe solvent is removed in vacuo
  5. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-a992423ab2704ff2a0a6058873d3a6cf
Source dataset
uspto-grants-1987_04
Patent number
US04661636

Reaction notes

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