Borane → HCID 22726863, compound

HRID 377395Notes

Reaction equation

HRID 377395 reaction equation
[SH:1][C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].B>C1COCC1>[OH:5][CH2:4][C:3]1[CH:7]=[CH:8][N:9]=[CH:10][C:2]=1[SH:1]

Participants

4

Reactant 2

HCID 6331BoraneHCID 127827583-Sulfanylpyridine-4-carboxylic acid

Product 1

HCID 22726863HCID 22726863, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3-mercaptoisonicotinic acid (1.80 g, 11.6 mmol) in dry THF (70 mL) was added slowly borane in THF (52 ml, 1M, 52 mmol) and the reaction mixture was stirred for 30 min. The solvent was evaporated under reduced pressure, methanol (40 mL) was added, and after gas evolution stopped, concentrated hydrochloric acid (3.6 mL) was added. The solution was filtered and the filtrate was evaporated to dryness. The residue was redissolved in a small volume of water, concentrated aqueous ammonia (3.6 ml) was added and the reaction mixture was evaporated to dryness. After overnight drying under vacuum, a quantitative yield of the title product was obtained, which was used for the next step without purification. 1H NMR (CD3OD) δ4.786 (s, 2H), 8.13 (d, 2H, J=6), 8.60 (d, 2H, J=6), 8.70 (s, 1H).

Workup

  1. customThe solvent was evaporated under reduced pressure, methanol (40 mL)
  2. additionwas added
  3. additionconcentrated hydrochloric acid (3.6 mL) was added
  4. filtrationThe solution was filtered
  5. customthe filtrate was evaporated to dryness
  6. dissolutionThe residue was redissolved in a small volume of water, concentrated aqueous ammonia (3.6 ml)
  7. additionwas added
  8. customthe reaction mixture was evaporated to dryness
  9. customAfter overnight drying under vacuum

Sources & evidence

ORD record
ord-bd578afa16134cc8a966b5fdbe6fcd50
Source dataset
uspto-grants-2000_02
Patent number
US06025352

Reaction notes

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