Hydrochloric Acid → HCID 9859267, compound

HRID 2289604Notes

Reaction equation

HRID 2289604 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[N:14]2[C:10](=[N:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=32)[S:9][N:8]=1)=[O:6].Cl>O1CCOCC1>[C:5]([C:7]1[N:14]2[C:10](=[N:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=32)[S:9][N:8]=1)([OH:6])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15888354HCID 15888354, compound

Product 1

HCID 9859267HCID 9859267, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 6 mL solution of 1N NaOH, 3-(methoxycarbonyl)-1,2,4-thiadiazolo[4,5-a]benzimidazole (1.0 g, 4.3 mmole) in 6 mL of dioxane, was added. The reaction mixture was stirred at room temperature until completion. The resulting mixture was then acidified with 3N HCl to pH ~2.0, and stirred at room temperature for an additional 0.5 h. The solid was filtered, washed with water, and dried under vacuum at 60° C. for 24 h to yield 0.74 g (78%) of the title compound as a colourless solid: mp 184-185° C. (dec); 1H NMR (DMSO-d6) δ 13.79 (br s, 1H), 8.59 (d, 1H), 7.78 (d, 1H), 7.51 (t, 1H), 7.40 (t, 1H); IR (KBr) ν 3435, 1705 cm-1 ; MS m/z 193 (M+ -OH), 175 (M+ -CO2)

Workup

  1. stirringstirred at room temperature for an additional 0.5 h
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried under vacuum at 60° C. for 24 h

Sources & evidence

ORD record
ord-81029cab1fbf4227b3149147b8c95ba9
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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