Water → HCID 15896060, compound

HRID 1953150Notes

Reaction equation

HRID 1953150 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+ -CH,CH(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-086b1610c2d2493893d66c4196eaeb47
Source dataset
uspto-grants-2000_09
Patent number
US06114537

Reaction notes

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