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

HRID 1296196Notes

Reaction equation

HRID 1296196 reaction equation
[NH2:1][CH:2]([CH2:5][OH:6])[CH2:3][OH:4].[CH3:7][O-:8].[Na+].CO[C:12]([C:14]1[CH:19]=[C:18]([NH2:20])[CH:17]=[C:16]([C:21]([O:23]C)=O)[CH:15]=1)=[O:13]>CO>[NH2:20][C:18]1[CH:19]=[C:14]([C:12]([NH:1][CH:2]([CH2:3][OH:4])[CH2:7][OH:8])=[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

5

Reactant 3

HCID 66831Dimethyl 5-aminoisophthalateHCID 68294SerinolHCID 10942334Sodium Methoxide

Product 1

HCID 99452455-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamideYield 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Amino-1,3-dihydroxypropane (27.4 g, 300 mmol) and 1.5M solution of sodium methylate in methanol (14.3 mL, 21.5 mmol) are added to a suspension of 5-amino-1,3-benzenedicarboxylic acid dimethyl ester (30.0 g, 143 mmol) in methanol (0.2 L). The reaction mixture is heated to the reflux temperature to get a solution. After 2.5 hours of reflux and 4 hours at room temperature the reaction mixture is filtered and the solid on filter is washed with methanol (40 mL) and dried yielding the product of the title (43.5 g, 133 mmol, yield: 93%).

Workup

  1. temperatureThe reaction mixture is heated to the reflux temperature
  2. customto get a solution
  3. filtrationis filtered
  4. filtrationthe solid on filter
  5. washis washed with methanol (40 mL)
  6. customdried
  7. customyielding the product of the title (43.5 g, 133 mmol, yield: 93%)

Sources & evidence

ORD record
ord-5a1341bed4614c468d89a9aaf9bf12f3
Source dataset
uspto-grants-2007_07
Patent number
US07244864B2

Reaction notes

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