Diglycolamine → HCID 57253850, compound

HRID 2184777Notes

Reaction equation

HRID 2184777 reaction equation
CO[C:3]([C:5]1[CH:10]=[N:9][C:8]([C:11]([O:13]C)=O)=[CH:7][N:6]=1)=[O:4].[NH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][OH:21]>C(O)C>[OH:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][NH:15][C:11]([C:8]1[CH:7]=[N:6][C:5]([C:3]([NH:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][OH:21])=[O:4])=[CH:10][N:9]=1)=[O:13]

Participants

4

Reactant 2

HCID 13578DiglycolamineHCID 518685Dimethyl pyrazine-2,5-dicarboxylate

Product 1

HCID 57253850HCID 57253850, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 500 mg of 2,5-dimethoxycarbonylpyrazine and 0.720 cm3 of 2-(2-aminoethoxy)ethanol in 3 cm3 of ethanol is heated at a temperature in the region of the reflux temperature for 4 hours. The reaction mixture is cooled to a temperature of 20° C. and the white solid formed is then filtered off and washed with twice 5 cm3 of ethanol. 150 mg of N,N′-bis(2-hydroxyethyloxyethyl)-pyrazine-2,5-dicarboxamide are thus obtained in the form of a white solid melting at 125° C. [1H NMR spectrum (300 MHz, (CD3)2SO-d6, δ at ppm): from 3.35 to 3.65 (mt, 16H: 2×NCH2CH2OCH2CH2O); 4.62 (t, J=5.5 Hz, 2H: 2×OH); 9.00 (t, J=6 Hz, 2H: 2×NHCO); 9.20 (s, 2H: ═CH at 3 and ═CH at 6)].

Workup

  1. customthe white solid formed
  2. filtrationis then filtered off
  3. washwashed with twice 5 cm3 of ethanol

Sources & evidence

ORD record
ord-049e5bcf658e43bfbe0d60f8d13af0ee
Source dataset
uspto-grants-2002_06
Patent number
US06399613B1

Reaction notes

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