Water → HCID 15896060, compound

HRID 2289603Notes

Reaction equation

HRID 2289603 reaction equation
[O:1]=[C:2]([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)[CH3:3].[BH4-].[Na+].O>CO>[OH:1][CH:2]([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)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10130628HCID 10130628, compound

Product 1

HCID 15896060HCID 15896060, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 3-(1-oxoethyl)-1,2,4-thiadiazolo[4,5-a]benzimidazole (729 mg, 3.36 mmol) in 200 mL methanol, was added sodium borohydride (140 mg, 3.69 mmol). The mixture was stirred for 30 min and 0.1 mL of water was added. The methanol was evaporated and the residue was partitioned between ethyl acetate and 0.1 M hydrochloric acid. The aqueous phase was extracted with ethyl acetate. The organic phases were combined, washed twice with brine, dried and evaporated. The crude residue was purified by chromatography using chloroform/methanol to give 3-(1-hydroxyethyl)-1,2,4-thiadiazolo[4,5-a]benzimidazole. mp 174-175° C.; 1H NMR (CDCl3) δ 8.05 (d, 1H), 7.80 (d, 1H), 7.47 (td, 1H), 7.36 (td, 1H), 5.39 (q, 1H), 2.76 (d, 1H), 1.84 (d, 3H) ppm; IR (KBr) ν 3136, 1544, 1494, 1478, 1451, 1374, 1250, 1200, 1123, 1103, 1093, 752, 729, 711 cm-1 ; MS m/z 219 (M+), 148 (M+ -CH3CH(OH)CN)

Workup

  1. customThe methanol was evaporated
  2. customthe residue was partitioned between ethyl acetate and 0.1 M hydrochloric acid
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washwashed twice with brine
  5. customdried
  6. customevaporated
  7. customThe crude residue was purified by chromatography

Sources & evidence

ORD record
ord-7f202c7d7a184d6ab4e62a1abc8abfec
Source dataset
uspto-grants-2000_07
Patent number
US06093738

Reaction notes

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