2-Methoxyethanol → HCID 178486869, compound

HRID 1784378Notes

Reaction equation

HRID 1784378 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9](C)[C:8](C)=[CH:7][C:3]=1[C:4](O)=[O:5].[C:13]([OH:16])(=O)C.[CH:17]([NH2:19])=N.[CH3:20][O:21]CCO>>[CH3:20][O:21][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][C:9]=1[O:16][CH3:13])[N:1]=[CH:17][N:19]=[C:4]2[OH:5]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 160693Formamidine acetateHCID 2665342-amino-4,5-dimethylbenzoic acid

Product 1

HCID 178486869HCID 178486869, compoundYield 86.2%

Procedure

2-amino-4,5-dimethylbenzoic acid (37)(5 g, 25.30 mmol) and formamidine acetate (5.2 g, 50.00 mmol) were dissolved in 2-methoxyethanol (80 ml) and the mixture heated to reflux for 16 hours. The mixture was cooled and concentrated in vacuo and suspended in a small volume of water. Sodium bicarbonate (5% aqueous solution) was added carefully (gas evolution) until pH 7 was attained. The suspension was filtered and the filtercake washed with water to give the title compound (4.50 g, 86.2%) as a brown powder which required no further purification. m/z (LC-MS, ESP): 207 [M+H]+, R/T=3.16 mins

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 16 hours
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated in vacuo
  5. additionSodium bicarbonate (5% aqueous solution) was added carefully (gas evolution) until pH 7
  6. filtrationThe suspension was filtered
  7. washthe filtercake washed with water

Sources & evidence

ORD record
ord-910ef591d58d402f9d4f2ab8fd7ea233
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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