Methanol → HCID 20627098, compound

HRID 2122051Notes

Reaction equation

HRID 2122051 reaction equation
C[O:2][C:3]([C:5]1[NH:9][C:8]([C:10]2[S:11][C:12]([C:15]3[NH:16][C:17]([C:20]([O:22]C)=[O:21])=[CH:18][CH:19]=3)=[CH:13][CH:14]=2)=[CH:7][CH:6]=1)=[O:4].CO.[OH-].[Na+]>O>[OH:4][C:3]([C:5]1[NH:9][C:8]([C:10]2[S:11][C:12]([C:15]3[NH:16][C:17]([C:20]([OH:22])=[O:21])=[CH:18][CH:19]=3)=[CH:13][CH:14]=2)=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 20627102HCID 20627102, compound

Product 1

HCID 20627098HCID 20627098, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of compound 5 (1.56 g, 4.73 mmol), methanol (125 mL), NaOH (30 g) and H2O (80 mL) was refluxed. The reaction was cooled to room temperature and the methanol was removed under reduced pressure. The mixture was poured into ice water and acidified slowly using 1 M HCl until a solid precipitate resulted. Filtration and drying produced 1.29 g (4.3 mmol, 90%) of the green title compound. 1H-NMR (d-DMSO): δ 7.33 (s, 1H), 6.81 (dd, 1H), 6.37 (dd, 1H). 13C-NMR: δ162.2, 134.6, 132.0, 125.1, 124.4, 117.1, 108.8.

Workup

  1. temperaturewas refluxed
  2. customthe methanol was removed under reduced pressure
  3. additionThe mixture was poured into ice water
  4. customresulted
  5. filtrationFiltration
  6. customdrying

Sources & evidence

ORD record
ord-2ce582ed65b3432bbf96bde0dc9541e4
Source dataset
uspto-grants-2004_02
Patent number
US06696575B2

Reaction notes

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