Hydrochloric Acid → HCID 178421814, compound

HRID 1432804Notes

Reaction equation

HRID 1432804 reaction equation
[CH3:1][C:2]1([CH3:13])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]#[N:12].[N-:14]=[N+:15]=[N-:16].[Na+].Cl>O1CCOCC1.[Br-].[Br-].[Zn+2]>[CH3:1][C:2]1([CH3:13])[CH:4]2[CH2:5][C:6]3[C:10]([CH:3]12)=[N:9][NH:8][C:7]=3[C:11]1[N:14]=[N:15][NH:16][N:12]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 33557Sodium AzideHCID 178421815(+/-)-1,1-dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile

Product 1

HCID 178421814HCID 178421814, compound

Reagents, catalysts & solvents 2

HCID 10421208Zinc bromideCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
200 °C

Procedure

(±)-1,1-Dimethyl-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene-4-carbonitrile (0.184 g, 1.06 mmol) was taken up in 1,4-dioxane (10 mL) with zinc dibromide (0.500 g, 2.22 mmol) and sodium azide (0.300 g, 4.62 mmol) in a heavy walled glass tube. The resulting solution was heated under microwave irradiation to 200° C. for 1 hour. The solution was poured into 1M aqueous hydrochloric acid (10 mL) and extracted into ethyl acetate (50 mL). Solvent was removed under reduced pressure and the resulting oil purified by preparative HPLC to give (±)-1,1-dimethyl-4-(2H-tetrazol-5-yl)-1a,3,5,5a-tetrahydro-1H-2,3-diaza-cyclopropa[a]pentalene as a white solid. m/z (ES+): 217 [M+H]+, 189 [M−N2+H]+; 1H NMR (CD3OD): δ 2.87 (dd, 1H, J1=16.5, J2=5.6), 2.67 (dd, 1H, J1=16.5, J2=0.8), 2.1-2.0 (m, 2H), 1.08 (s, 3H), 0.69 (s, 3H).

Workup

  1. extractionextracted into ethyl acetate (50 mL)
  2. customSolvent was removed under reduced pressure
  3. customthe resulting oil purified by preparative HPLC

Sources & evidence

ORD record
ord-cc060f2cc9b84753ba137980303ed6f2
Source dataset
uspto-grants-2009_11
Patent number
US07612106B2

Reaction notes

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