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

HRID 1296198Notes

Reaction equation

HRID 1296198 reaction equation
C(O[C:6]([C:8]1[CH:13]=[C:12]([NH2:14])[CH:11]=[C:10]([C:15]([O:17]CCCC)=O)[CH:9]=1)=[O:7])CCC.[CH3:22][O-:23].[Na+].[NH2:25][CH:26]([CH2:29][OH:30])[CH2:27][OH:28]>CO>[NH2:14][C:12]1[CH:13]=[C:8]([C:6]([NH:25][CH:26]([CH2:27][OH:28])[CH2:22][OH:23])=[O:7])[CH:9]=[C:10]([C:15]([NH:25][CH:26]([CH2:29][OH:30])[CH2:27][OH:28])=[O:17])[CH:11]=1

Participants

5

Reactant 3

HCID 68294SerinolHCID 10942334Sodium MethoxideHCID 117379291,3-Benzenedicarboxylic acid, 5-amino-, dibutyl ester

Product 1

HCID 99452455-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamideYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
25 °C

Procedure

5-Amino-1,3-benzenedicarboxylic acid di-n-butyl ester (1148 g, 3.91 mol) is loaded into a 10 L reaction vessel containing methanol (7.5 L) and a 1.5M solution of sodium methylate in methanol (0.39 L, 0.59 mol) and 2-amino-1,3-dihydroxypropane (820 g, 9.0 mol) are added thereto. The reaction mixture is then heated to the reflux temperature and kept at this temperature for 4 hours. The mixture is then concentrated to 4 L, cooled to 25° C. and after one night at room temperature it is filtered. The solid on filter is washed with methanol (2×1.3 L) and dried yielding the compound of the title (1215 g, 3.71 mol, yield: 95%).

Workup

  1. temperatureThe reaction mixture is then heated to the reflux temperature
  2. concentrationThe mixture is then concentrated to 4 L
  3. filtrationis filtered
  4. filtrationThe solid on filter
  5. washis washed with methanol (2×1.3 L)
  6. customdried
  7. customyielding the compound of the title (1215 g, 3.71 mol, yield: 95%)

Sources & evidence

ORD record
ord-4f535afabcd64d78ad6af3aaa28117ca
Source dataset
uspto-grants-2007_07
Patent number
US07244864B2

Reaction notes

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