Hydrochloric Acid → (5-Phenyl-1,2,4-thiadiazol-3-yl)methanol

HRID 1424348Notes

Reaction equation

HRID 1424348 reaction equation
[C:1]1([C:7]2[S:11][N:10]=[C:9]([C:12](OCC)=[O:13])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)C.[BH4-].[Na+].Cl>>[C:1]1([C:7]2[S:11][N:10]=[C:9]([CH2:12][OH:13])[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 12351254Ethyl 5-phenyl-1,2,4-thiadiazole-3-carboxylate

Product 1

HCID 86700894(5-Phenyl-1,2,4-thiadiazol-3-yl)methanolYield 13.2%

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 5-phenyl-1,2,4-thiadiazole-3-carboxylate (Example 7A, 230 mg, 0.982 mmol) in anhydrous ethanol (3 mL, 51.4 mmol) was added NaBH4 (149 mg, 3.93 mmol) at 0° C. The reaction mixture was heated to 80° C. for 30 min, then HCl 1N (1 mL) was added and ethanol was evaporated. Dichloromethane was added to the reaction followed by brine and this was extracted with dichloromethane (3×). The organic layers were dried over anhydrous magnesium sulfate and concentrated. The residue was purified on silica gel column chromatography (100% CH2Cl2 up to 10% EtOAc/CH2Cl2) to provide the title material (25 mgs, 13%). LC (Method B): 1.858 min. LCMS (APCI) calcd for C9H9N2OS [M+H]+ m/z 193.04. found 193.0. 1H NMR (CDCl3, 400 MHz) δ ppm: 7.89-8.03 (m, 2H), 7.46-7.62 (m, 3H), 4.99 (d, J=5.87 Hz, 2H), 2.81 (t, J=6.06 Hz, 1H)

Workup

  1. customethanol was evaporated
  2. additionDichloromethane was added to the reaction
  3. extractionthis was extracted with dichloromethane (3×)
  4. dry with materialThe organic layers were dried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel column chromatography (100% CH2Cl2 up to 10% EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-2a4b4cf483614ea384bb42882e4879ba
Source dataset
uspto-grants-2015_01
Patent number
US08927688B2

Reaction notes

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