Water → HCID 19977094, compound

HRID 1450476Notes

Reaction equation

Br[CH2:2][C:3]1[C:4]2[CH:11]=[C:10]([C:12]3[N:13]=[N:14][N:15]([CH3:17])[N:16]=3)[CH:9]=[CH:8][C:5]=2[S:6][CH:7]=1.[C-:18]#[N:19].[Na+].O>CS(C)=O>[C:18]([CH2:2][C:3]1[C:4]2[CH:11]=[C:10]([C:12]3[N:13]=[N:14][N:15]([CH3:17])[N:16]=3)[CH:9]=[CH:8][C:5]=2[S:6][CH:7]=1)#[N:19]

Participants

Conditions

Temperature: 100 °C

Procedure

The crude 3-bromomethyl-5-(2-methyl-tetrazol-5-yl)benzo[b]thiophene (0.145 g) in DMSO (0.3 ml) was added to a mixture of sodium cyanide (29.9 mg, 0.6 mmol) in DMSO (0.2 ml) and the mixture was stirred at 100° C. for 2 h. After cooling, the mixture was poured into water (10 ml) and a brown solid was filtered off, washed with water and dried in a vacuum pistol to leave 73.5 mg. The filtrate was extracted with dichloromethane (3×30 ml) and the combined extracts were dried (Na2SO4) and evaporated in vacuo to leave 44.7 mg. This was combined with the original solid and chromatographed on flash silica, eluting with 20-50% ethyl acetate/petroleum ether to yield 61.5 mg (38%) of the title product as a white solid. δ (CDCl3) 3.99 (2H, s), 4.43 (3H, s), 7.59 (1H, s), 8.00 (1H, d, J=8.5 Hz), 8.19 (1H, dd, J=8.5 and 1.5 Hz), 8.47 (1H, s).

Workup

temperatureAfter cooling
filtrationa brown solid was filtered off
washwashed with water
customdried in a vacuum pistol
customto leave 73.5 mg
extractionThe filtrate was extracted with dichloromethane (3×30 ml)
dry with materialthe combined extracts were dried (Na2SO4)
customevaporated in vacuo
customto leave 44.7 mg
customchromatographed on flash silica
washeluting with 20-50% ethyl acetate/petroleum ether

Sources & evidence

ORD record: ord-fdd3ea64626f48c0abaec2fa4676edfa
Source dataset: uspto-grants-1997_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05602162

Reaction notes

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