Hydrochloric Acid → HCID 178421814、化合物

HRID 1432804ノート

反応式

HRID 1432804 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 178421814HCID 178421814、化合物

試薬・触媒・溶媒 2

HCID 10421208Zinc bromide触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
200 °C

実験手順

(±)-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).

後処理

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

出典と根拠

ORDレコード
ord-cc060f2cc9b84753ba137980303ed6f2
出典データセット
uspto-grants-2009_11
特許番号
US07612106B2

反応ノート

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