Dimethyl Sulfoxide → HCID 19977108, compound

HRID 2399713Notes

Reaction equation

HRID 2399713 reaction equation
Br[C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[C-:17]#[N:18].[Na+].O.[CH3:21]S(C)=O>>[C:17]([CH2:21][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:15]([CH3:16])[N:14]=[N:13][N:12]=3)[CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1)#[N:18]

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 8929Sodium CyanideHCID 19977110HCID 19977110, compound

Product 1

HCID 19977108HCID 19977108, compoundYield 4%

Procedure

The crude 3-bromo-5-(1-methyltetrazol-5-yl)benzo[b]thiophene (0.504 g) was reacted with 97.7 mg (1.99 mmol) of sodium cyanide in 1.5 ml of DMSO at 100° C. for 2 h. After cooling, the reaction mixture was poured into water (25 ml) and extracted with dichloromethane (6×50 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo to leave 0.37 g. Chromatography on flash silica, eluting with 30-60% ethyl acetate/petroleum ether yielded 28.0 mg (4%) of the title product. δ (CDCl3) 4.00 (2H, s), 4.23 (3H, s), 7.63 (1H, s), 7.73 (1H, dd), 8.08 (1H, d), 8.15 (1H, d).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with dichloromethane (6×50 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customevaporated in vacuo
  5. customto leave 0.37 g
  6. washChromatography on flash silica, eluting with 30-60% ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-4b57402af0f64c5b8f710fd443b67fea
Source dataset
uspto-grants-1995_09
Patent number
US05451588

Reaction notes

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