Sodium Hydroxide → HCID 23711126, compound

HRID 2289605Notes

Reaction equation

HRID 2289605 reaction equation
[C:1]([C:4]1[N:11]2[C:7](=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=32)[S:6][N:5]=1)([OH:3])=[O:2].[OH-].[Na+:17]>CO.O>[C:1]([C:4]1[N:11]2[C:7](=[N:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=32)[S:6][N:5]=1)([O-:3])=[O:2].[Na+:17]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9859267HCID 9859267, compound

Product 1

HCID 23711126HCID 23711126, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 3-carboxy-1,2,4-thiadiazolo[4,5-a]benzimidazole (10.00 g, 45.62 mmol) in methanol (150 ml) and water (100 ml), 1M NaOH (45.6 ml) was added over a period of 1 h. After 4 h, the solution turned clear and the methanol was removed under reduced pressure. The aqueous solution was extracted with chloroform, the aqueous phase was freeze-dried to give the title compound (10.4 g, 95%) as a white solid: mp 225-227° C.; 1H NMR (DMSO-d6) δ 7.68 (d, 1H), 7.05 (d, 1H), 6.95 (t, 1H), 6.80 (t, 1H) ppm; 13C NMR (DMSO-d6) δ 167.20, 161.76, 149.68, 148.84, 129.52, 126.23, 122.74, 118.37, 116.06 ppm; IR (KBr) ν 3395, 3243, 1663, 1641, 1522, 1443, 1334, 827, 729 cm-1.

Workup

  1. additionwas added over a period of 1 h
  2. customthe methanol was removed under reduced pressure
  3. extractionThe aqueous solution was extracted with chloroform
  4. customthe aqueous phase was freeze-dried

Sources & evidence

ORD record
ord-487a0f5cfbdb4782b69d2e8336ed0f34
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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