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

HRID 1296195Notes

Reaction equation

CO[C:3]([C:5]1[CH:10]=[C:9]([NH2:11])[CH:8]=[C:7]([C:12]([O:14]C)=O)[CH:6]=1)=[O:4].[NH2:16][CH:17]([CH2:20][OH:21])[CH2:18][OH:19]>CO>[NH2:11][C:9]1[CH:10]=[C:5]([C:3]([NH:16][CH:17]([CH2:20][OH:21])[CH2:18][OH:19])=[O:4])[CH:6]=[C:7]([C:12]([NH:16][CH:17]([CH2:20][OH:21])[CH2:18][OH:19])=[O:14])[CH:8]=1

Participants

Conditions

Temperature: 105 °C

Procedure

5-Amino-1,3-benzenedicarboxylic acid dimethyl ester (40.0 g, 191 mmol) and 2-amino-1,3-dihydroxypropane (104.5 g, 1.147 mol) are loaded into a 1 L vessel equipped with a mechanical stirrer, a thermometer and a refluxing refrigerator. The suspension is heated up to 105° C., and is maintained at this temperature for 150 minutes to yield a solution. After cooling to 50° C., methanol (0.7 L) is added and the obtained suspension is maintained for 4 hours at room temperature. The solid that separates is filtered, washed with methanol (0.3 L), and dried in the oven at 45° C. for 4 hours yielding the compound of the title (56.3 g, 0.172 mol, yield: 90%).

Workup

customequipped with a mechanical stirrer
temperatureis maintained at this temperature for 150 minutes
customto yield a solution
temperatureAfter cooling to 50° C.
temperaturethe obtained suspension is maintained for 4 hours at room temperature
filtrationThe solid that separates is filtered
washwashed with methanol (0.3 L)
customdried in the oven at 45° C. for 4 hours
customyielding the compound of the title (56.3 g, 0.172 mol, yield: 90%)

Sources & evidence

ORD record: ord-6abc1cb076a7426eaa6a68c2012b415d
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244864B2

Reaction notes

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