Serinol → 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamide

HRID 1296197Notes

Reaction equation

HRID 1296197 reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].C(O[C:12]([C:14]1[CH:19]=[C:18]([NH2:20])[CH:17]=[C:16]([C:21]([O:23]CCCC)=O)[CH:15]=1)=[O:13])CCC>C(O)CCC>[NH2:20][C:18]1[CH:19]=[C:14]([C:12]([NH:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4])=[O:13])[CH:15]=[C:16]([C:21]([NH:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4])=[O:23])[CH:17]=1

Participants

4

Reactant 2

HCID 68294SerinolHCID 117379291,3-Benzenedicarboxylic acid, 5-amino-, dibutyl ester

Product 1

HCID 99452455-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamideYield 96%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-amino-1,3-dihydroxypropane (31 g, 340 mmol) and 5-amino-1,3-benzenedicarboxylic acid di-n-butyl ester (20.0 g, 68.2 mmol) is heated to 125° C. for 3 hours while the n-butyl alcohol which forms is distilled off. After cooling the reaction mixture to about 70° C. the solution is diluted with methanol (0.35 L) and a solid product crystallizes out. After 4 hours at room temperature the mixture is filtered and the solid on filter is washed with methanol (30 mL) and dried yielding the compound of the title (21.4 g, 65.5 mmol, yield: 96%).

Workup

  1. distillationforms is distilled off
  2. additionis diluted with methanol (0.35 L)
  3. customa solid product crystallizes out
  4. filtrationAfter 4 hours at room temperature the mixture is filtered
  5. filtrationthe solid on filter
  6. washis washed with methanol (30 mL)
  7. customdried
  8. customyielding the compound of the title (21.4 g, 65.5 mmol, yield: 96%)

Sources & evidence

ORD record
ord-7d39dde8de56484da300757d486ea6ff
Source dataset
uspto-grants-2007_07
Patent number
US07244864B2

Reaction notes

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