Hydrochloric Acid → HCID 178421814, 화합물

HRID 1295070노트

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HRID 1295070 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 178421814HCID 178421814, 화합물

시약·촉매·용매 2

HCID 10421208Zinc bromide촉매HCID 312751,4-Dioxane용매

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온도
200 °C

실험 절차

(±)-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).

후처리

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

출처 및 근거

ORD 기록
ord-81d4115e240e492f935cb6244420307b
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241792B2

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