p-Toluenesulfonic acid → Hexamethylolmelamine

HRID 1534619Notes

Reaction equation

HRID 1534619 reaction equation
[CH2:1]([N:3]([CH2:20][OH:21])[C:4]1[N:9]=[C:8]([N:10]([CH2:13][OH:14])[CH2:11][OH:12])[N:7]=[C:6]([N:15]([CH2:18][OH:19])[CH2:16][OH:17])[N:5]=1)[OH:2].OCC1C=CN=NN=1.C(=O)(OCCC)N.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[CH2:13]([N:10]([CH2:11][OH:12])[C:8]1[N:9]=[C:4]([N:3]([CH2:1][OH:2])[CH2:20][OH:21])[N:5]=[C:6]([N:15]([CH2:18][OH:19])[CH2:16][OH:17])[N:7]=1)[OH:14]

Participants

4

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 12306Propyl carbamateHCID 19909967HCID 19909967, compound

Product 1

HCID 62361Hexamethylolmelamine

Conditions

Temperature
95 °C

Procedure

The general procedure of Example 1 is repeated, substituting the hydroxymethyltriazine Hexamethylolmelamine (10.0 g, 0.0327 mole), n-propyl carbamate (20.2 g, 0.196 mole), and para-toluenesulfonic acid (0.60 g, 0.0035 mole) are stirred at 95° C. in a flask equipped with a vacuum distillation head. During 30 minutes, the pressure is lowered in stages to 50 mm Hg., and 3.24 g. of distillate (mostly water, 92% of theoretical) is collected in the distillate receiver. At room temperature, the product in the reaction vessel is a gray-white solid. The infrared spectrum shows little or no residual hydroxyl functionality and is similar to the spectrum of authentic hexa-n-propylcarbamylmethylated melamine, made by Example 1. The general formula is, approximately:

Workup

  1. customequipped with a vacuum distillation head
  2. distillationof distillate (mostly water, 92% of theoretical) is collected in the distillate receiver
  3. customAt room temperature

Sources & evidence

ORD record
ord-e64f4a544c4046078725040d416ce9fe
Source dataset
uspto-grants-1992_02
Patent number
US05089561

Reaction notes

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