Azidotrimethylsilane → HCID 9964175, compound

HRID 2375872Notes

Reaction equation

HRID 2375872 reaction equation
[N:1]([Si](C)(C)C)=[N+:2]=[N-:3].[NH2:8][C:9]1[CH:10]=[C:11]([C:15]#[CH:16])[CH:12]=[CH:13][CH:14]=1>>[N:1]1[NH:2][N:3]=[C:15]([C:11]2[CH:10]=[C:9]([NH2:8])[CH:14]=[CH:13][CH:12]=2)[CH:16]=1

Participants

3

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 9964175HCID 9964175, compound

Conditions

Temperature
150 °C

Procedure

The mixture of azidotrimethylsilane (137 μL, 1.03 mmol) and 3-amino-phenylacetylene (117 mg, 1.00 mmol) was heated in a sealed tube at 150° C. for 16 h. After that time, the mixture was cooled down and triturated by EtOAc/hexane (50%, 10 mL). The mother liquor was purified by TLC eluting with 7% MeOH/CH2Cl2. to give the title compound as brown oil. 1H NMR (CD3OD, 400 MHz): δ=6.61-6.64 (m, 1H), 7.01-7.09 (m, 3H), 7.94 (s, 1H). MS (ES+): m/z 161.20 (38) [MH+]. HPLC: tR=1.54 min (ZQ2000, polar—5 min).

Workup

  1. temperatureAfter that time, the mixture was cooled down
  2. customtriturated by EtOAc/hexane (50%, 10 mL)
  3. customThe mother liquor was purified by TLC
  4. washeluting with 7% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-8b1c2b049c534ec4b9f0cd41af58c940
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

Loading…